Organic electroluminescent device comprising delayed fluorescent materials

ABSTRACT

An organic electroluminescent device containing a cathode, an anode, and one or more organic layers containing plural light emitting materials between the cathode and the anode, wherein the organic electroluminescent device is a multiple wavelength light emitting organic electroluminescent device emitting light from the plural light emitting materials, and which is designed so that light that has the shortest wavelength contains delayed fluorescent light can improve light emission efficiency of a short wavelength light and color tone and has a large degree of freedom in design and a simple structure.

TECHNICAL FIELD

The present invention relates to a multiple wavelength light emittingorganic electroluminescent device.

BACKGROUND ART

Studies have been actively performed on an organic electroluminescentdevice having a structure containing a cathode, an anode, and a lightemitting layer containing a light emitting material that is formedbetween the anode and the cathode. Most of the studies are to develop amonochrome light emitting organic electroluminescent device by addingone light emitting material having a particular light emissionwavelength to the light emitting layer, and some of them are to developa multiple wavelength light emitting organic electroluminescent deviceby using plural light emitting materials that have different lightemission wavelengths. For example, such one has been studied that alight emitting layer containing a blue light emitting material, a lightemitting layer containing a green light emitting material and a lightemitting layer containing a red light emitting material are formed, andwhite light emission is to be achieved by mixing light emission from thelight emitting materials.

Patent Document 1 describes an organic electroluminescent device havinga light emitting layer containing a blue or blue-green fluorescent lightemitting material and a light emitting layer containing a phosphorescentlight emitting material other than blue, in which the lowest excitationtriplet energy level of the fluorescent light emitting material islarger than the lowest excitation triplet energy level of thephosphorescent light emitting material. In the examples thereof, such anorganic electroluminescent device is described that contains an anode, ahole transporting layer, a hole-side intermediate layer, an orange-redlight emitting layer, a blue light emitting layer, a green lightemitting layer, an electron-side intermediate layer, an electrontransporting layer, and a cathode, which are formed in this order. Theblue light emitting layer is formed of α-NPD, the orange-red lightemitting layer is doped with iridium(III)bis(2-methyldibenzo[f,h]quinoxaline (acetylacetonate) as a lightemitting material, and the green light emitting layer is doped withfac-tris(2-phenylpyridine) iridium ((Ir(ppy)₃)). However, PatentDocument 1 does not describe the use of a delayed fluorescent material.

Patent Document 2 describes an organic electroluminescent device havinga light emitting layer containing a green light emitting layercontaining a green delayed fluorescent material formed in contact with ahole transporting layer, a red phosphorescent light emitting layercontaining a red light emitting material formed in contact with thegreen light emitting layer, and a blue light emitting layer containing ablue light emitting material formed in contact with the red lightemitting layer. The organic electroluminescent device is designed insuch a manner that the HOMO of the green delayed fluorescent material isdeeper than the HOMO of the material of the hole transporting layer andis shallower than the HOMO of the red phosphorescent light emittingmaterial. Patent Document 2 described that according to the design, thebarrier between the HOMOs of the hole transporting layer and the greenlight emitting layer is reduced, and thus red phosphorescent light maybe emitted with a high efficiency.

CITATION LIST Patent Documents

-   Patent Document 1: JP-A-2012-89513-   Patent Document 2: JP-A-2010-114070

SUMMARY OF INVENTION Technical Problem

As described above, some studies have been made to develop a multiplewavelength light emitting organic electroluminescent device by usingplural light emitting materials having different light emissionwavelengths. However, the organic electroluminescent device described inPatent Document 1 fails to make the internal quantum efficiency of bluefluorescent light from the blue fluorescent material exceeding 25%, andthus has a problem of an insufficient blue light intensity. This is theprincipled limitation, and thus the problem cannot be solved as long asthe constitution of Patent Document 1 is employed. On the other hand,the organic electroluminescent device described in Patent Document 2 mayenhance the light emission efficiency of red phosphorescent light, butthere is no suggestion relating to the effective enhancement of thelight emission efficiency of light having a short wavelength, such asblue light. Furthermore, there are many structural limitations, forexample, the green light emitting layer is necessarily formed on themost anode-side.

Under the current technical situation, the present inventors have madeinvestigations for providing a multiple wavelength light emittingorganic electroluminescent device that is improved in color tone throughthe enhancement of the light emission efficiency of light having arelatively short wavelength, such as blue light, and has a large degreeof freedom in design to achieve a simple structure.

Solution to Problem

As a result of earnest investigations performed, the inventors havefound that the intended multiple wavelength light emitting organicelectroluminescent device may be provided by utilizing delayedfluorescent light to satisfy the particular condition. The organicelectroluminescent device developed by the inventors is based on theunprecedented technological concept and has high practical usefulnessdue to the large degree of freedom thereof. Based on the knowledge, theinventors thus provide the invention described below as a measure forsolving the problem.

(1) An organic electroluminescent device containing a cathode, an anode,and one or more organic layers containing plural light emittingmaterials between the cathode and the anode, wherein the organicelectroluminescent device is a multiple wavelength light emittingorganic electroluminescent device emitting light from the plural lightemitting materials, and in the light thus emitted from the lightemitting materials, light that has the shortest wavelength containsdelayed fluorescent light.

(2) The organic electroluminescent device according to the item (1),wherein the light emitting material that emits light having the shortestwavelength also functions as a host material of another light emittingmaterial, or forms one of the organic layers alone.

(3) The organic electroluminescent device according to the item (1) or(2), wherein the light emitting material that emits light having theshortest wavelength has an energy difference (ΔE_(ST)) between thelowest excitation triplet energy level and the lowest excitation singletenergy level at 5 K of 0.3 eV or less.

(4) The organic electroluminescent device according to any one of theitems (1) to (3), wherein the light emitting material that emits light,having the shortest wavelength is a blue light emitting material.

(5) The organic electroluminescent device according to any one of theitems (1) to (4), wherein the light emitting material that emits lighthaving the shortest wavelength has a light emission intensity of morethan 20% based on the total light emission.

(6) The organic electroluminescent device according to any one of theitems (1) to (5), wherein one of the organic layers contains the lightemitting material that emits light having the shortest wavelength and atleast one kind of a light emitting material that emits light having adifferent wavelength, and the light emitting material that emits lighthaving the shortest wavelength also functions as a host material.

(7) The organic electroluminescent device according to any one of theitems (1) to (5), wherein one of the organic layers contains the lightemitting material that emits light having the shortest wavelength and atleast two kinds of light emitting materials that each emit light havinga different wavelength, and the light emitting material that emits lighthaving the shortest wavelength also functions as a host material.

(8) The organic electroluminescent device according to any one of theitems (1) to (7), wherein the light emitting material that emits lighthaving the shortest wavelength forms at least one layer of the organiclayers alone.

(9) The organic electroluminescent device according to any one of theitems (1) to (8), wherein the organic electroluminescent device containstwo or more layers each containing a light emitting material, and amongthe layers, a layer that is the closest to the cathode and a layer thatis the closest to the anode each contain the light emitting materialthat emits light having the shortest wavelength.

(10) The organic electroluminescent device according to the claim (9),wherein the organic electroluminescent device, contains a layer thatcontains the light emitting material that emits light having theshortest wavelength as a host material between the layer that is theclosest to the cathode and the layer that is the closest to the anode.

(11) The organic electroluminescent device according to any one of theitems (1) to (10), wherein the organic electroluminescent devicecontains a layer containing a blue light emitting material doped with agreen light emitting material or a red light emitting material.

(12) The organic electroluminescent device according to any one of theitems (1) to (10), wherein the organic electroluminescent devicecontains a laminate of a layer containing a blue light emittingmaterial, a layer containing a blue light emitting material doped with agreen light emitting material or a red light emitting material, and alayer containing a blue light emitting material.

(13) The organic electroluminescent device according to any one of theitems (1) to (12), wherein the plural light emitting materials contain ablue light emitting material, a green light emitting material, and a redlight emitting material.

(14) The organic electroluminescent device according to any one of theitems (1) to (13), wherein the organic electroluminescent devicecontains a layer containing a blue tight emitting material doped with agreen light emitting material and a red light emitting material.

(15) The organic electroluminescent device according to any one of theitems (1) to (14), wherein the organic electroluminescent devicecontains a laminate of a layer containing a green light emittingmaterial, a layer containing a green light emitting material doped witha red light emitting material, and a layer containing a blue lightemitting material.

(16) The organic electroluminescent device according to any one of theitems (1) to (15), wherein all the plural light emitting materials emitdelayed fluorescent light.

(17) The organic electroluminescent device according to any one of theitems (1) to (15), wherein at least one of the plural light emittingmaterials emits phosphorescent light.

(18) The organic electroluminescent device according to any one of theitems (1) to (17), wherein the organic electroluminescent device emitswhite light through color mixing of light emitted from the plural lightemitting materials.

Advantageous Effects of Invention

In the multiple wavelength light emitting organic electroluminescentdevice of the invention, the light emitting material that emits lighthaving the shortest wavelength also emits delayed fluorescent light.Accordingly, the color tone may be improved even though the lightemission efficiency of the light having a short wavelength, such as bluelight, is enhanced. According to the organic electroluminescent device,of the invention, the intended multiple wavelength light emittingorganic electroluminescent device may be produced due to the largedegree of freedom in design and the simple structure thereof.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic illustration showing the mechanism of lightemission in the invention.

FIG. 2 is a schematic cross sectional illustration showing examples ofthe structure of the light emitting layer of the organicelectroluminescent device of the invention.

FIG. 3 is a schematic cross sectional illustration showing examples ofthe structure of the light emitting layer of the organicelectroluminescent device of the invention.

FIG. 4 is a schematic cross sectional illustration showing examples ofthe structure of the light emitting layer of the organicelectroluminescent device of the invention.

FIG. 5 is a schematic cross sectional illustration showing examples ofthe structure of the light emitting layer of the organicelectroluminescent device of the invention.

FIG. 6 is a schematic cross sectional illustration showing examples ofthe structure of the light emitting layer of the organicelectroluminescent device of the invention.

FIG. 7 is a schematic cross sectional illustration showing an example ofthe layer structure of the organic electroluminescent device.

FIG. 8 is a graph showing the light emission spectra of the organicelectroluminescent device of Example 1.

FIG. 9 is a graph showing the electric current density-external quantumefficiency characteristics of the organic electroluminescent device ofExample 1.

FIG. 10 is a graph showing the energy band diagram of the organicelectroluminescent device of Example 1.

FIG. 11 is a graph showing the light emission spectra of the organicelectroluminescent devices of Examples 2 to 4.

FIG. 12 is a graph showing the electric current density-external quantumefficiency characteristics of the organic electroluminescent devices ofExamples 2 to 4.

FIG. 13 is a graph showing the energy band diagram of the organicelectroluminescent devices of Examples 2 to 4.

FIG. 14 is a graph showing the light emission spectrum of the organicelectroluminescent device of Example 5.

FIG. 15 is a graph showing the electric current density-external quantumefficiency characteristics of the organic electroluminescent device ofExample 5.

FIG. 16 is a graph showing the energy band diagram of the organicelectroluminescent device of Example 5.

FIG. 17 is a graph showing the light, emission spectra of the organicelectroluminescent device A of Example 6.

FIG. 18 is a graph showing the voltage-electric current densitycharacteristics of the organic electroluminescent devices A to C ofExamples 6 to 8.

FIG. 19 is a graph showing the electric current density-external quantumefficiency characteristics of the organic electroluminescent devices Ato G of Examples 6 to 8.

FIG. 20 is a graph showing the energy band diagram of the organicelectroluminescent devices of Examples 6 to 8.

FIG. 21 is a graph showing the light emission spectra of the organicelectroluminescent devices D to F of Examples 9 to 11.

FIG. 22 is a graph showing the voltage-electric current densitycharacteristics of the organic electroluminescent devices D to F ofExamples 9 to 11.

FIG. 23 is a graph showing the electric current density-external quantumefficiency characteristics of the organic electroluminescent devices Dto F of Examples 9 to 11.

DESCRIPTION OF EMBODIMENTS

The contents of the invention will be described in detail below. Theconstitutional elements may be described below with reference torepresentative embodiments and specific examples of the invention, butthe invention is not limited to the embodiments and the examples. In thedescription, a numerical range expressed with reference to theexpressions, an upper limit or less and/or a lower limit or more, meansa range that includes the upper limit and/or the lower limit.

Basic Structure of Organic Electroluminescent Device

The multiple wavelength light emitting organic electroluminescent deviceof the invention contains at least a cathode, an anode, and one or moreorganic layers intervening therebetween. The one or more organic layersformed may contain at least one layer, and the one or more organiclayers contain plural light emitting materials. The plural lightemitting materials may be contained in different organic layers or maybe contained in the same organic layer. For example, in the case wherethree kinds of light emitting materials, i.e., a blue light emittingmaterial, a green light emitting material and a red light emittingmaterial, are used, the three light emitting materials may be containedin one light, emitting layer, or may be contained in each of threeorganic layers, respectively. Furthermore, a particular light emittingmaterial may be contained in plural organic layers. In the organicelectroluminescent device of the invention, the plural light emittingmaterials each emit light, and thus the device functions as a multiplewavelength light emitting device.

In the description of the invention, a light emitting material that hasa maximum light emission wavelength in a range of 400 nm or more and 490nm or less is referred to as a blue light emitting material, a lightemitting material that has a maximum light emission wavelength in arange of more than 490 nm and 580 nm or less is referred to as a greenlight emitting material, and a light emitting material that has amaximum light emission wavelength in a range of more than 580 nm and 700nm or less is referred to as a red light emitting material.

Delayed Fluorescent Light

In the organic electroluminescent device of the invention, the lightthat has the shortest wavelength in the light emitted from the lightemitting materials contained in the device contains delayed fluorescentlight. The delayed fluorescent light may be emitted by selecting a lightemitting material that emits delayed fluorescent light (i.e., a delayedfluorescent material) as a light emitting material, and using thematerial in the organic electroluminescent device. The use of thedelayed fluorescent material may enhance the light emission efficiencyat the fluorescent wavelength of the delayed fluorescent material. Theprinciple of the features may be described as follows.

In an organic electroluminescent device, carriers are injected from ananode and a cathode, to a light emitting material to form an excitedstate for the light emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescent device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy use efficiency. However, the excited tripletstate has a long lifetime and thus causes saturation of the excitedstate and deactivation of energy through mutual action with the excitonsin the excited triplet state, and therefore the quantum yield ofphosphorescence may generally be often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescentdevice. In the case where a delayed fluorescent material is used in anorganic electroluminescent device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited single state hasthe same wavelength as fluorescent light since it is light emission fromthe excited single state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited single state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.The delayed fluorescent material preferably has an energy difference(ΔE_(ST)) between the lowest excitation triplet energy level and thelowest excitation singlet energy level at 77° K of 0.2 eV or less, andmore preferably 0.1 eV or less.

In the organic electroluminescent device of the invention, such a lightemitting material that emits delayed fluorescent light is selected asthe light emitting material that emits light having the shortestwavelength. According to the procedure, not only the light emissionefficiency at the light emission wavelength thereof is drasticallyenhanced, but also an advantage is obtained that the excitons in theexcited triplet state are transferred to the excited triplet state ofanother (second) light emitting material emitting light having a longerwavelength, so as to enhance the light emission efficiency of the secondlight emitting material as shown in FIG. 1. The second light emittingmaterial may be one emitting phosphorescent light and may be oneemitting fluorescent light, and in the case where the second lightemitting material is a delayed fluorescent material, the second lightemitting material may emit delayed fluorescent light. In the case wherea delayed fluorescent material is selected as the second light emittingmaterial, the light emission efficiency of the second light emittingmaterials may be drastically enhanced through the same mechanism asdescribed above. As the second light emitting material referred herein,not only one kind thereof but also two or more kinds thereof may beused.

FIG. 1 is an illustration showing, as one example, an embodiment usingthree light emitting materials, i.e., a blue light emitting material, agreen light emitting material and a red light emitting material. In theembodiment described herein, all the three light emitting materials aredelayed fluorescent materials, but in the invention, it is sufficientthat only the blue light emitting material, which is the light emittingmaterial emitting light having a shortest wavelength, is a delayedfluorescent material. In other words, the green light emitting materialand the red light emitting material may be an ordinary phosphorescentlight emitting material, and one of them may be a delayed fluorescentmaterial, whereas the other may be a phosphorescent light emittingmaterial. In the embodiment shown in FIG. 1, a delayed fluorescentmaterial is used as the blue light emitting material, and thus bluedelayed fluorescent light (TADF) is emitted, along with ordinary bluefluorescent light (Fluo), thereby the blue light emission efficiency isdrastically enhanced. Furthermore, the excitons in the excited tripletstate of the blue light emitting material are transferred to the excitedtriplet state of the green light emitting material and the excitedtriplet state of the red light emitting material, and thereby the lightemitting materials each emit phosphorescent light and delayedfluorescent light. According to the embodiment employed, the blue colortone may be improved while enhancing the quantum efficiency. The bluelight emission, the green light emission and the red light emission maybe recognized as white light emission through color mixing.

The kind of the delayed fluorescent material that may be used in theinvention is not particularly limited, and may be selected from onescapable of emitting delayed fluorescent light in consideration of thelight emission wavelength. A delayed fluorescent material generally hasa structure containing an acceptor moiety (A) and a donor moiety (D)bonded to each other. The numbers of the acceptor moiety and the donormoiety each may be one or more, and the number of the acceptor moietyand the number of the donor moiety in one molecule may be the same as ordifferent from each other. For example, there are delayed fluorescentmaterials having various structures, such as an A-D type, an A-(D)_(n)type, an (A)_(n)-D type and an -(A-D)_(n)-type, wherein n represents aninteger of 2 or more, and may be, for example, an integer of from 2 to6.

The molecular weight of the delayed fluorescent material is preferably1,500 or less, more preferably 1,200 or less, further preferably 1,000or less, and still further preferably 800 or less, in the case where alight emitting layer is intended to be formed as a film by a vapordeposition method. The delayed fluorescent material may be formed into afills by a coating method irrespective of the molecular weight thereof.The compound that has a relatively large molecular weight may be formedinto a film by a coating method.

Specific examples of the preferred delayed fluorescent material that maybe used in the invention are shown below, but the delayed fluorescentmaterial that may be used in the invention is not construed as beinglimited to the examples.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (101). The entire description of WO 2013/154064including the paragraphs 0008 to 0048 and 0095 to 0133 is incorporatedherein by reference.

wherein in the general formula (101), at least one of R¹ to represents acyano group, at least one of R¹ to R⁵ represents a group represented bythe following general formula (111), and the balance of R¹ to R⁵ eachrepresent a hydrogen atom or a substituent,

wherein in the general formula (111), R²¹ to R²⁸ each Independentlyrepresent, a hydrogen atom or a substituent, provided that at least oneof the following conditions (A) and (B) is satisfied:

(A) R²⁵ and R²⁶ together form a single bond, and

(B) R²⁷ and R²⁸ together represent an atomic group that is necessary forforming a substituted or unsubstituted benzene ring.

In the general formula (101), at least one of R¹ to R⁵ preferablyrepresents a group represented by any one of the following generalformulae (112) to (115).

wherein in the general formula (112), to R³¹ to R³⁸ each independentlyrepresent a hydrogen atom or a substituent.

wherein in the general formula (113), R⁴¹ to R⁴⁶ each independentlyrepresent a hydrogen atom or a substituent,

wherein in the general formula (114), R⁵¹ to R⁶² each independentlyrepresent a hydrogen atom or a substituent,

wherein in the general formula (115), R⁷¹ to R⁸⁰ each independentlyrepresent a hydrogen atom or a substituent.

Specific examples of the compounds include the compounds shown in thefollowing tables. In the case where two or more groups represented byany one of the general formulae (112) to (115) are present in themolecule of the following example compounds, all the groups have thesame structure. The formulae (121) to (124) in the tables represent thefollowing formulae, respectively, and n represents the number of therepeating units.

TABLE 1-1 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 1 General General CNGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 2 General General CN General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 3 General General CNGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 4 General General CN General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 5 General General CNGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 6 General General CN General General H H t-C₄H₉ H formula(112) formula (112) formula (112) formula (112) 7 General General CNGeneral General H H Cl H formula (112) formula (112) formula (112)formula (112) 8 General General CN General General H H F H formula (112)formula (112) formula (112) formula (112) 9 General General CN GeneralGeneral H H H CH₃ formula (112) formula (112) formula (112) formula(112) 10 General General CN General General H H H CH₃O formula (112)formula (112) formula (112) formula (112) 11 General General CN GeneralH H H H H formula (112) formula (112) formula (112) 12 General GeneralCN General H H CH₃ H H formula (112) formula (112) formula (112) 13General General CN General H H CH₃O H H formula (112) formula (112)formula (112) 14 General General CN General H H H CH₃ H formula (112)formula (112) formula (112) 15 General General CN General H H H CH₃O Hformula (112) formula (112) formula (112) 16 General General CN GeneralH H H t-C₄H₉ H formula (112) formula (112) formula (112) 17 GeneralGeneral CN General H H H Cl H formula (112) formula (112) formula (112)18 General General CN General H H H F H formula (112) formula (112)formula (112) 19 General General CN General H H H H CH₃ formula (112)formula (112) formula (112) 20 General General CN General H H H H CH₃Oformula (112) formula (112) formula (112) 21 General General CN H H H HH H formula (112) formula (112) 22 General General CN H H H CH₃ H Hformula (112) formula (112) 23 General General CN H H H CH₃O H H formula(112) formula (112) 24 General General CN H H H H CH₃ H formula (112)formula (112) 25 General General CN H H H H CH₃O H formula (112) formula(112) 26 General General CN H H H H t-C₄H₉ H formula (112) formula (112)27 General General CN H H H H Cl H formula (112) formula (112) 28General General CN H H H H F H formula (112) formula (112) 29 GeneralGeneral CN H H H H H CH₃ formula (112) formula (112) 30 General GeneralCN H H H H H CH₃O formula (112) formula (112) 31 General H CN General HH H H H formula (112) formula (112) 32 General H CN General H H CH₃ H Hformula (112) formula (112) 33 General H CN General H H CH₃O H H formula(112) formula (112) 34 General H CN General H H H CH₃ H formula (112)formula (112) 35 General H CN General H H H CH₃O H formula (112) formula(112) 36 General H CN General H H H t-C₄H₉ H formula (112) formula (112)37 General H CN General H H H Cl H formula (112) formula (112) 38General H CN General H H H F H formula (112) formula (112) 39 General HCN General H H H H CH₃ formula (112) formula (112) 40 General H CNGeneral H H H H CH₃O formula (112) formula (112) 41 General H CN HGeneral H H H H formula (112) formula (112) 42 General H CN H General HCH₃ H H formula (112) formula (112) 43 General H CN H General H CH₃O H Hformula (112) formula (112) 44 General H CN H General H H CH₃ H formula(112) formula (112) 45 General H CN H General H H CH₃O H formula (112)formula (112) 46 General H CN H General H H t-C₄H₉ H formula (112)formula (112) 47 General H CN H General H H Cl H formula (112) formula(112) 48 General H CN H General H H F H formula (112) formula (112) 49General H CN H General H H H CH₃ formula (112) formula (112) 50 GeneralH CN H General H H H CH₃O formula (112) formula (112) 51 General H CN HH H H H H formula (112) 52 General H CN H H H CH₃ H H formula (112) 53General H CN H H H CH₃O H H formula (112) 54 General H CN H H H H CH₃ Hformula (112) 55 General H CN H H H H CH₃O H formula (112) 56 General HCN H H H H t-C₄H₉ H formula (112) 57 General H CN H H H H Cl H formula(112) 58 General H CN H H H H F H formula (112) 59 General H CN H H H HH CH₃ formula (112) 60 General H CN H H H H H CH₃O formula (112)

TABLE 1-2 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 61 General General CNGeneral F H H H H formula (112) formula (112) formula (112) 62 GeneralGeneral CN General F H CH₃ H H formula (112) formula (112) formula (112)63 General General CN General F H CH₃O H H formula (112) formula (112)formula (112) 64 General General CN General F H H CH₃ H formula (112)formula (112) formula (112) 65 General General CN General F H H CH₃O Hformula (112) formula (112) formula (112) 66 General General CN GeneralF H H t-C₄H₉ H formula (112) formula (112) formula (112) 67 GeneralGeneral CN General F H H Cl H formula (112) formula (112) formula (112)68 General General CN General F H H F H formula (112) formula (112)formula (112) 69 General General CN General F H H H CH₃ formula (112)formula (112) formula (112) 70 General General CN General F H H H CH₃Oformula (112) formula (112) formula (112) 71 General General CN F F H HH H formula (112) formula (112) 72 General General CN F F H CH₃ H Hformula (112) formula (112) 73 General General CN F F H CH₃O H H formula(112) formula (112) 74 General General CN F F H H CH₃ H formula (112)formula (112) 75 General General CN F F H H CH₃O H formula (112) formula(112) 76 General General CN F F H H t-C₄H₉ H formula (112) formula (112)77 General General CN F F H H Cl H formula (112) formula (112) 78General General CN F F H H F H formula (112) formula (112) 79 GeneralGeneral CN F F H H H CH₃ formula (112) formula (112) 80 General GeneralCN F F H H H CH₃O formula (112) formula (112) 81 General F CN General FH H H H formula (112) formula (112) 82 General F CN General F H CH₃ H Hformula (112) formula (112) 83 General F CN General F H CH₃O H H formula(112) formula (112) 84 General F CN General F H H CH₃ H formula (112)formula (112) 85 General F CN General F H H CH₃O H formula (112) formula(112) 86 General F CN General F H H t-C₄H₉ H formula (112) formula (112)87 General F CN General F H H Cl H formula (112) formula (112) 88General F CN General F H H F H formula (112) formula (112) 89 General FCN General F H H H CH₃ formula (112) formula (112) 90 General F CNGeneral F H H H CH₃O formula (112) formula (112) 91 General F CN FGeneral H H H H formula (112) formula (112) 92 General F CN F General HCH₃ H H formula (112) formula (112) 93 General F CN F General H CH₃O H Hformula (112) formula (112) 94 General F CN F General H H CH₃ H formula(112) formula (112) 95 General F CN F General H H CH₃O H formula (112)formula (112) 96 General F CN F General H H t-C₄H₉ H formula (112)formula (112) 97 General F CN F General H H Cl H formula (112) formula(112) 98 General F CN F General H H F H formula (112) formula (112) 99General F CN F General H H H CH₃ formula (112) formula (112) 100 GeneralF CN F General H H H CH₃O formula (112) formula (112) 101 General F CN FF H H H H formula (112) 102 General F CN F F H CH₃ H H formula (112) 103General F CN F F H CH₃O H H formula (112) 104 General F CN F F H H CH₃ Hformula (112) 105 General F CN F F H H CH₃O H formula (112) 106 GeneralF CN F F H H t-C₄H₉ H formula (112) 107 General F CN F F H H Cl Hformula (112) 108 General F CN F F H H F H formula (112) 109 General FCN F F H H H CH₃ formula (112) 110 General F CN F F H H H CH₃O formula(112)

TABLE 1-3 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 111 General General CNGeneral OH H H H H formula (112) formula (112) formula (112) 112 GeneralGeneral CN General OH H CH₃ H H formula (112) formula (112) formula(112) 113 General General CN General OH H CH₃O H H formula (112) formula(112) formula (112) 114 General General CN General OH H H CH₃ H formula(112) formula (112) formula (112) 115 General General CN General OH H HCH₃O H formula (112) formula (112) formula (112) 116 General General CNGeneral OH H H t-C₄H₉ H formula (112) formula (112) formula (112) 117General General CN General OH H H Cl H formula (112) formula (112)formula (112) 118 General General CN General OH H H F H formula (112)formula (112) formula (112) 119 General General CN General OH H H H CH₃formula (112) formula (112) formula (112) 120 General General CN GeneralOH H H H CH₃O formula (112) formula (112) formula (112) 121 GeneralGeneral CN OH OH H H H H formula (112) formula (112) 122 General GeneralCN OH OH H CH₃ H H formula (112) formula (112) 123 General General CN OHOH H CH₃O H H formula (112) formula (112) 124 General General CN OH OH HH CH₃ H formula (112) formula (112) 125 General General CN OH OH H HCH₃O H formula (112) formula (112) 126 General General CN OH OH H Ht-C₄H₉ H formula (112) formula (112) 127 General General CN OH OH H H ClH formula (112) formula (112) 128 General General CN OH OH H H F Hformula (112) formula (112) 129 General General CN OH OH H H H CH₃formula (112) formula (112) 130 General General CN OH OH H H H CH₃Oformula (112) formula (112) 131 General OH CN General OH H H H H formula(112) formula (112) 132 General OH CN General OH H CH₃ H H formula (112)formula (112) 133 General OH CN General OH H CH₃O H H formula (112)formula (112) 134 General OH CN General OH H H CH₃ H formula (112)formula (112) 135 General OH CN General OH H H CH₃O H formula (112)formula (112) 136 General OH CN General OH H H t-C₄H₉ H formula (112)formula (112) 137 General OH CN General OH H H Cl H formula (112)formula (112) 138 General OH CN General OH H H F H formula (112) formula(112) 139 General OH CN General OH H H H CH₃ formula (112) formula (112)140 General OH CN General OH H H H CH₃O formula (112) formula (112) 141General OH CN OH General H H H H formula (112) formula (112) 142 GeneralOH CN OH General H CH₃ H H formula (112) formula (112) 143 General OH CNOH General H CH₃O H H formula (112) formula (112) 144 General OH CN OHGeneral H H CH₃ H formula (112) formula (112) 145 General OH CN OHGeneral H H CH₃O H formula (112) formula (112) 146 General OH CN OHGeneral H H t-C₄H₉ H formula (112) formula (112) 147 General OH CN OHGeneral H H Cl H formula (112) formula (112) 148 General OH CN OHGeneral H H F H formula (112) formula (112) 149 General OH CN OH GeneralH H H CH₃ formula (112) formula (112) 150 General OH CN OH General H H HCH₃O formula (112) formula (112) 151 General OH CN OH OH H H H H formula(112) 152 General OH CN OH OH H CH₃ H H formula (112) 153 General OH CNOH OH H CH₃O H H formula (112) 154 General OH CN OH OH H H CH₃ H formula(112) 155 General OH CN OH OH H H CH₃O H formula (112) 156 General OH CNOH OH H H t-C₄H₉ H formula (112) 157 General OH CN OH OH H H Cl Hformula (112) 158 General OH CN OH OH H H F H formula (112) 159 GeneralOH CN OH OH H H H CH₃ formula (112) 160 General OH CN OH OH H H H CH₃Oformula (112) 161 General General CN General Cl H H H H formula (112)formula (112) formula (112) 162 General General CN General Cl H CH₃ H Hformula (112) formula (112) formula (112) 163 General General CN GeneralCl H CH₃O H H formula (112) formula (112) formula (112) 164 GeneralGeneral CN General Cl H H CH₃ H formula (112) formula (112) formula(112) 165 General General CN General Cl H H CH₃O H formula (112) formula(112) formula (112) 166 General General CN General Cl H H t-C₄H₉ Hformula (112) formula (112) formula (112) 167 General General CN GeneralCl H H Cl H formula (112) formula (112) formula (112) 168 GeneralGeneral CN General Cl H H F H formula (112) formula (112) formula (112)169 General General CN General Cl H H H CH₃ formula (112) formula (112)formula (112) 170 General General CN General Cl H H H CH₃O formula (112)formula (112) formula (112) 171 General General CN General F H H H Hformula (112) formula (112) formula (112) 172 General General CN GeneralF H CH₃ H H formula (112) formula (112) formula (112) 173 GeneralGeneral CN General F H CH₃O H H formula (112) formula (112) formula(112) 174 General General CN General F H H CH₃ H formula (112) formula(112) formula (112) 175 General General CN General F H H CH₃O H formula(112) formula (112) formula (112)

TABLE 1-4 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 176 General General CNGeneral F H H t-C₄H₉ H formula (112) formula (112) formula (112) 177General General CN General F H H Cl H formula (112) formula (112)formula (112) 178 General General CN General F H H F H formula (112)formula (112) formula (112) 179 General General CN General F H H H CH₃formula (112) formula (112) formula (112) 180 General General CN GeneralF H H H CH₃O formula (112) formula (112) formula (112) 181 GeneralGeneral CN General CH₃O H H H H formula (112) formula (112) formula(112) 182 General General CN General CH₃O H CH₃ H H formula (112)formula (112) formula (112) 183 General General CN General CH₃O H CH₃O HH formula (112) formula (112) formula (112) 184 General General CNGeneral CH₃O H H CH₃ H formula (112) formula (112) formula (112) 185General General CN General CH₃O H H CH₃O H formula (112) formula (112)formula (112) 186 General General CN General CH₃O H H t-C₄H₉ H formula(112) formula (112) formula (112) 187 General General CN General CH₃O HH Cl H formula (112) formula (112) formula (112) 188 General General CNGeneral CH₃O H H F H formula (112) formula (112) formula (112) 189General General CN General C₂H₅O H H H CH₃ formula (112) formula (112)formula (112) 190 General General CN General C₂H₅O H H H CH₃O formula(112) formula (112) formula (112) 191 General General CN General C₂H₅O HH H H formula (112) formula (112) formula (112) 192 General General CNGeneral C₂H₅O H CH₃ H H formula (112) formula (112) formula (112) 193General General CN General C₂H₅O H CH₃O H H formula (112) formula (112)formula (112) 194 General General CN General C₂H₅O H H CH₃ H formula(112) formula (112) formula (112) 195 General General CN General C₂H₅O HH CH₃O H formula (112) formula (112) formula (112) 196 General GeneralCN General C₂H₅O H H t-C₄H₉ H formula (112) formula (112) formula (112)197 General General CN General C₂H₅O H H Cl H formula (112) formula(112) formula (112) 198 General General CN General C₂H₅O H H F H formula(112) formula (112) formula (112) 199 General General CN General C₂H₅O HH H CH₃ formula (112) formula (112) formula (112) 200 General General CNGeneral C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 201General General CN General C₆H₅O H H H H formula (112) formula (112)formula (112) 202 General General CN General C₆H₅O H CH₃ H H formula(112) formula (112) formula (112) 203 General General CN General C₆H₅O HCH₃O H H formula (112) formula (112) formula (112) 204 General GeneralCN General C₆H₅O H H CH₃ H formula (112) formula (112) formula (112) 205General General CN General C₆H₅O H H CH₃O H formula (112) formula (112)formula (112) 206 General General CN General C₆H₅O H H t-C₄H₉ H formula(112) formula (112) formula (112) 207 General General CN General C₆H₅O HH Cl H formula (112) formula (112) formula (112) 208 General General CNGeneral C₆H₅O H H F H formula (112) formula (112) formula (112) 209General General CN General C₆H₅O H H H CH₃ formula (112) formula (112)formula (112) 210 General General CN General C₆H₅O H H H CH₃O formula(112) formula (112) formula (112) 211 General General CN General Formula(121) H H H H formula (112) formula (112) formula (112) 212 GeneralGeneral CN General Formula (121) H CH₃ H H formula (112) formula (112)formula (112) 213 General General CN General Formula (121) H CH₃O H Hformula (112) formula (112) formula (112) 214 General General CN GeneralFormula (121) H H CH₃ H formula (112) formula (112) formula (112) 215General General CN General Formula (121) H H CH₃O H formula (112)formula (112) formula (112) 216 General General CN General Formula (121)H H t-C₄H₉ H formula (112) formula (112) formula (112) 217 GeneralGeneral CN General Formula (121) H H Cl H formula (112) formula (112)formula (112) 218 General General CN General Formula (121) H H F Hformula (112) formula (112) formula (112) 219 General General CN GeneralFormula (121) H H H CH₃ formula (112) formula (112) formula (112) 220General General CN General Formula (121) H H H CH₃O formula (112)formula (112) formula (112) 221 General General CN General Formula (122)H H H H formula (112) formula (112) formula (112) 222 General General CNGeneral Formula (122) H CH₃ H H formula (112) formula (112) formula(112) 223 General General CN General Formula (122) H CH₃O H H formula(112) formula (112) formula (112) 224 General General CN General Formula(122) H H CH₃ H formula (112) formula (112) formula (112) 225 GeneralGeneral CN General Formula (122) H H CH₃O H formula (112) formula (112)formula (112) 226 General General CN General Formula (122) H H t-C₄H₉ Hformula (112) formula (112) formula (112) 227 General General CN GeneralFormula (122) H H Cl H formula (112) formula (112) formula (112) 228General General CN General Formula (122) H H F H formula (112) formula(112) formula (112) 229 General General CN General Formula (122) H H HCH₃ formula (112) formula (112) formula (112) 230 General General CNGeneral Formula (122) H H H CH₃O formula (112) formula (112) formula(112) 231 General General CN General Formula (123) H H H H formula (112)formula (112) formula (112) 232 General General CN General Formula (123)H CH₃ H H formula (112) formula (112) formula (112) 233 General GeneralCN General Formula (123) H CH₃O H H formula (112) formula (112) formula(112) 234 General General CN General Formula (123) H H CH₃ H formula(112) formula (112) formula (112) 235 General General CN General Formula(123) H H CH₃O H formula (112) formula (112) formula (112) 236 GeneralGeneral CN General Formula (123) H H t-C₄H₉ H formula (112) formula(112) formula (112) 237 General General CN General Formula (123) H H ClH formula (112) formula (112) formula (112) 238 General General CNGeneral Formula (123) H H F H formula (112) formula (112) formula (112)239 General General CN General Formula (123) H H H CH₃ formula (112)formula (112) formula (112) 240 General General CN General Formula (123)H H H CH₃O formula (112) formula (112) formula (112)

TABLE 1-5 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 241 General General CNGeneral Formula (124) H H H H formula (112) formula (112) formula (112)242 General General CN General Formula (124) H CH₃ H H formula (112)formula (112) formula (112) 243 General General CN General Formula (124)H CH₃O H H formula (112) formula (112) formula (112) 244 General GeneralCN General Formula (124) H H CH₃ H formula (112) formula (112) formula(112) 245 General General CN General Formula (124) H H CH₃O H formula(112) formula (112) formula (112) 246 General General CN General Formula(124) H H t-C₄H₉ H formula (112) formula (112) formula (112) 247 GeneralGeneral CN General Formula (124) H H Cl H formula (112) formula (112)formula (112) 248 General General CN General Formula (124) H H F Hformula (112) formula (112) formula (112) 249 General General CN GeneralFormula (124) H H H CH₃ formula (112) formula (112) formula (112) 250General General CN General Formula (124) H H H CH₃O formula (112)formula (112) formula (112) 251 General General CN General General HC₆H₅ H H formula (112) formula (112) formula (112) formula (112) 252General General CN General General H H C₅H₆ H formula (112) formula(112) formula (112) formula (112) 253 General General CN General H HC₆H₅ H H formula (112) formula (112) formula (112) 254 General GeneralCN General H H H C₅H₆ H formula (112) formula (112) formula (112) 255General General CN H H H C₆H₅ H H formula (112) formula (112) 256General General CN H H H H C₆H₅ H formula (112) formula (112) 257General H CN General H H C₆H₅ H H formula (112) formula (112) 258General H CN General H H H C₆H₅ H formula (112) formula (112) 259General H CN H General H C₆H₅ H H formula (112) formula (112) 260General H CN H General H H C₆H₅ H formula (112) formula (112) 261General H CN H H H C₆H₅ H H formula (112) 262 General H CN H H H H C₆H₅H formula (112) 263 General General CN General F H C₆H₅ H H formula(112) formula (112) formula (112) 264 General General CN General F H HC₆H₅ H formula (112) formula (112) formula (112) 265 General General CNF F H C₆H₅ H H formula (112) formula (112) 266 General General CN F F HH C₆H₅ H formula (112) formula (112) 267 General F CN General F H C₆H₅ HH formula (112) formula (112) 268 General F CN General F H H C₆H₅ Hformula (112) formula (112) 269 General F CN F General H C₆H₅ H Hformula (112) formula (112) 270 General F CN F General H H C₆H₅ Hformula (112) formula (112) 271 General F CN F F H C₆H₅ H H formula(112) 272 General F CN F F H H C₆H₅ H formula (112) 273 General GeneralCN General OH H C₆H₅ H H formula (112) formula (112) formula (112) 274General General CN General OH H H C₆H₅ H formula (112) formula (112)formula (112) 275 General General CN OH OH H C₆H₅ H H formula (112)formula (112) 276 General General CN OH OH H H C₆H₅ H formula (112)formula (112) 277 General OH CN General OH H C₆H₅ H H formula (112)formula (112) 278 General OH CN General OH H H C₆H₅ H formula (112)formula (112) 279 General OH CN OH General H C₆H₅ H H formula (112)formula (112) 280 General OH CN OH General H H C₆H₅ H formula (112)formula (112) 281 General OH CN OH OH H C₆H₅ H H formula (112) 282General OH CN OH OH H H C₆H₅ H formula (112) 283 General General CNGeneral Cl H C₆H₅ H H formula (112) formula (112) formula (112) 284General General CN General Cl H H C₆H₅ H formula (112) formula (112)formula (112) 285 General General CN General F H C₆H₅ H H formula (112)formula (112) formula (112) 286 General General CN General F H H C₆H₅ Hformula (112) formula (112) formula (112) 287 General General CN GeneralCH₃O H C₆H₅ H H formula (112) formula (112) formula (112) 288 GeneralGeneral CN General CH₃O H H C₆H₅ H formula (112) formula (112) formula(112) 289 General General CN General C₂H₃O H C₆H₅ H H formula (112)formula (112) formula (112) 290 General General CN General C₂H₃O H HC₆H₅ H formula (112) formula (112) formula (112) 291 General General CNGeneral C₆H₅O H C₆H₅ H H formula (112) formula (112) formula (112) 292General General CN General C₆H₅O H H C₆H₅ H formula (112) formula (112)formula (112) 293 General General CN General Formula (121) H C₆H₅ H Hformula (112) formula (112) formula (112) 294 General General CN GeneralFormula (121) H H C₆H₅ H formula (112) formula (112) formula (112) 295General General CN General Formula (122) H C₆H₅ H H formula (112)formula (112) formula (112) 296 General General CN General Formula (122)H H C₆H₅ H formula (112) formula (112) formula (112) 297 General GeneralCN General Formula (123) H C₆H₅ H H formula (112) formula (112) formula(112) 298 General General CN General Formula (123) H H C₆H₅ H formula(112) formula (112) formula (112) 299 General General CN General Formula(124) H C₆H₅ H H formula (112) formula (112) formula (112) 300 GeneralGeneral CN General Formula (124) H H C₆H₅ H formula (112) formula (112)formula (112)

TABLE 2-1 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 301 General CN GeneralGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 302 General CN General General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 303 General CN GeneralGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 304 General CN General General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 305 General CN GeneralGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 306 General CN General General General H H t-C₄H₉ Hformula (112) formula (112) formula (112) formula (112) 307 General CNGeneral General General H H Cl H formula (112) formula (112) formula(112) formula (112) 308 General CN General General General H H F Hformula (112) formula (112) formula (112) formula (112) 309 General CNGeneral General General H H H CH₃ formula (112) formula (112) formula(112) formula (112) 310 General CN General General General H H H CH₃Oformula (112) formula (112) formula (112) formula (112) 311 General CNGeneral General H H H H H formula (112) formula (112) formula (112) 312General CN General General H H H CH₃ H formula (112) formula (112)formula (112) 313 General CN General General H H H CH₃O H formula (112)formula (112) formula (112) 314 General CN General H General H H H Hformula (112) formula (112) formula (112) 315 General CN General HGeneral H H CH₃ H formula (112) formula (112) formula (112) 316 GeneralCN General H General H H CH₃O H formula (112) formula (112) formula(112) 317 General CN H General General H H H H formula (112) formula(112) formula (112) 318 General CN H General General H H CH₃ H formula(112) formula (112) formula (112) 319 General CN H General General H HCH₃O H formula (112) formula (112) formula (112) 320 H CN GeneralGeneral General H H H H formula (112) formula (112) formula (112) 321 HCN General General General H H CH₃ H formula (112) formula (112) formula(112) 322 H CN General General General H H CH₃O H formula (112) formula(112) formula (112) 323 General CN General H H H H H H formula (112)formula (112) 324 General CN General H H H H CH₃ H formula (112) formula(112) 325 General CN General H H H H CH₃O H formula (112) formula (112)326 General CN H General H H H H H formula (112) formula (112) 327General CN H General H H H CH₃ H formula (112) formula (112) 328 GeneralCN H General H H H CH₃O H formula (112) formula (112) 329 H CN GeneralGeneral H H H H H formula (112) formula (112) 330 H CN General General HH H CH₃ H formula (112) formula (112) 331 H CN General General H H HCH₃O H formula (112) formula (112) 332 General CN H H General H H H Hformula (112) formula (112) 333 General CN H H General H H CH₃ H formula(112) formula (112) 334 General CN H H General H H CH₃O H formula (112)formula (112) 335 H CN General H General H H H H formula (112) formula(112) 336 H CN General H General H H CH₃ H formula (112) formula (112)337 H CN General H General H H CH₃O H formula (112) formula (112) 338 HCN H General General H H H H formula (112) formula (112) 339 H CN HGeneral General H H CH₃ H formula (112) formula (112) 340 H CN H GeneralGeneral H H CH₃O H formula (112) formula (112) 341 General CN H H H H HH H formula (112) 342 General CN H H H H H CH₃ H formula (112) 343General CN H H H H H CH₃O H formula (112) 344 H CN General H H H H H Hformula (112) 345 H CN General H H H H CH₃ H formula (112) 346 H CNGeneral H H H H CH₃O H formula (112) 347 H CN H General H H H H Hformula (112) 348 H CN H General H H H CH₃ H formula (112) 349 H CN HGeneral H H H CH₃O H formula (112) 350 General CN General General F H HH H formula (112) formula (112) formula (112) 351 General CN GeneralGeneral F H H CH₃ H formula (112) formula (112) formula (112) 352General CN General General F H H CH₃O H formula (112) formula (112)formula (112) 353 General CN General F General H H H H formula (112)formula (112) formula (112) 354 General CN General F General H H CH₃ Hformula (112) formula (112) formula (112) 355 General CN General FGeneral H H CH₃O H formula (112) formula (112) formula (112) 356 GeneralCN F General General H H H H formula (112) formula (112) formula (112)357 General CN F General General H H CH₃ H formula (112) formula (112)formula (112) 358 General CN F General General H H CH₃O H formula (112)formula (112) formula (112) 359 F CN General General General H H H Hformula (112) formula (112) formula (112) 360 F CN General GeneralGeneral H H CH₃ H formula (112) formula (112) formula (112)

TABLE 2-2 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 361 F CN General GeneralGeneral H H CH₃O H formula (112) formula (112) formula (112) 362 GeneralCN General F F H H H H formula (112) formula (112) 363 General CNGeneral F F H H CH₃ H formula (112) formula (112) 364 General CN GeneralF F H H CH₃O H formula (112) formula (112) 365 General CN F General F HH H H formula (112) formula (112) 366 General CN F General F H H CH₃ Hformula (112) formula (112) 367 General CN F General F H H CH₃O Hformula (112) formula (112) 368 F CN General General F H H H H formula(112) formula (112) 369 F CN General General F H H CH₃ H formula (112)formula (112) 370 F CN General General F H H CH₃O H formula (112)formula (112) 371 General CN F F General H H H H formula (112) formula(112) 372 General CN F F General H H CH₃ H formula (112) formula (112)373 General CN F F General H H CH₃O H formula (112) formula (112) 374 FCN General F General H H H H formula (112) formula (112) 375 F CNGeneral F General H H CH₃ H formula (112) formula (112) 376 F CN GeneralF General H H CH₃O H formula (112) formula (112) 377 F CN F GeneralGeneral H H H H formula (112) formula (112) 378 F CN F General General HH CH₃ H formula (112) formula (112) 379 F CN F General General H H CH₃OH formula (112) formula (112) 380 General CN F F F H H H H formula (112)381 General CN F F F H H CH₃ H formula (112) 382 General CN F F F H HCH₃O H formula (112) 383 F CN General F F H H H H formula (112) 384 F CNGeneral F F H H CH₃ H formula (112) 385 F CN General F F H H CH₃O Hformula (112) 386 F CN F General F H H H H formula (112) 387 F CN FGeneral F H H CH₃ H formula (112) 388 F CN F General F H H CH₃O Hformula (112) 389 General CN General General OH H H H H formula (112)formula (112) formula (112) 390 General CN General General OH H H CH₃ Hformula (112) formula (112) formula (112) 391 General CN General GeneralOH H H CH₃O H formula (112) formula (112) formula (112) 392 General CNGeneral OH General H H H H formula (112) formula (112) formula (112) 393General CN General OH General H H CH₃ H formula (112) formula (112)formula (112) 394 General CN General OH General H H CH₃O H formula (112)formula (112) formula (112) 395 General CN General OH General H H t-C₄H₉H formula (112) formula (112) formula (112) 396 General CN General OHGeneral H H Cl H formula (112) formula (112) formula (112) 397 GeneralCN General OH General H H F H formula (112) formula (112) formula (112)398 General CN OH General General H H H H formula (112) formula (112)formula (112) 399 General CN OH General General H H CH₃ H formula (112)formula (112) formula (112) 400 General CN OH General General H H CH₃O Hformula (112) formula (112) formula (112) 401 OH CN General GeneralGeneral H H H H formula (112) formula (112) formula (112) 402 OH CNGeneral General General H H CH₃ H formula (112) formula (112) formula(112) 403 OH CN General General General H H CH₃O H formula (112) formula(112) formula (112) 404 General CN General OH OH H H H H formula (112)formula (112) 405 General CN General OH OH H H CH₃ H formula (112)formula (112) 406 General CN General OH OH H H CH₃O H formula (112)formula (112) 407 General CN OH General OH H H H H formula (112) formula(112) 408 General CN OH General OH H H CH₃ H formula (112) formula (112)409 General CN OH General OH H H CH₃O H formula (112) formula (112) 410OH CN General General OH H H H H formula (112) formula (112) 411 OH CNGeneral General OH H H CH₃ H formula (112) formula (112) 412 OH CNGeneral General OH H H CH₃O H formula (112) formula (112) 413 General CNOH OH General H H H H formula (112) formula (112) 414 General CN OH OHGeneral H H CH₃ H formula (112) formula (112) 415 General CN OH OHGeneral H H CH₃O H formula (112) formula (112) 416 OH CN General OHGeneral H H H H formula (112) formula (112) 417 OH CN General OH GeneralH H CH₃ H formula (112) formula (112) 418 OH CN General OH General H HCH₃O H formula (112) formula (112) 419 OH CN OH General General H H H Hformula (112) formula (112) 420 OH CN OH General General H H CH₃ Hformula (112) formula (112) 421 OH CN OH General General H H CH₃O Hformula (112) formula (112) 422 General CN OH OH OH H H H H formula(112) 423 General CN OH OH OH H H CH₃ H formula (112) 424 General CN OHOH OH H H CH₃O H formula (112) 425 OH CN General OH OH H H H H formula(112)

TABLE 2-3 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 426 OH CN General OH OH H HCH₃ H formula (112) 427 OH CN General OH OH H H CH₃O H formula (112) 428OH CN OH General OH H H H H formula (112) 429 OH CN OH General OH H HCH₃ H formula (112) 430 OH CN OH General OH H H CH₃O H formula (112) 431OH CN OH OH General H H H H formula (112) 432 OH CN OH OH General H HCH₃ H formula (112) 433 OH CN OH OH General H H CH₃O H formula (112) 434General CN General Cl General H H H H formula (112) formula (112)formula (112) 435 General CN General Cl General H H CH₃ H formula (112)formula (112) formula (112) 436 General CN General Cl General H H CH₃O Hformula (112) formula (112) formula (112) 437 General CN General ClGeneral H H t-C₄H₉ H formula (112) formula (112) formula (112) 438General CN General Cl General H H Cl H formula (112) formula (112)formula (112) 439 General CN General Cl General H H F H formula (112)formula (112) formula (112) 440 General CN General F General H H H Hformula (112) formula (112) formula (112) 441 General CN General FGeneral H H CH₃ H formula (112) formula (112) formula (112) 442 GeneralCN General F General H H CH₃O H formula (112) formula (112) formula(112) 443 General CN General F General H H t-C₄H₉ H formula (112)formula (112) formula (112) 444 General CN General F General H H Cl Hformula (112) formula (112) formula (112) 445 General CN General FGeneral H H F H formula (112) formula (112) formula (112) 446 General CNGeneral CH₃O General H H H H formula (112) formula (112) formula (112)447 General CN General CH₃O General H H CH₃ H formula (112) formula(112) formula (112) 448 General CN General CH₃O General H H CH₃O Hformula (112) formula (112) formula (112) 449 General CN General CH₃OGeneral H H t-C₄H₉ H formula (112) formula (112) formula (112) 450General CN General CH₃O General H H Cl H formula (112) formula (112)formula (112) 451 General CN General CH₃O General H H F H formula (112)formula (112) formula (112) 452 General CN General C₂H₅O General H H H Hformula (112) formula (112) formula (112) 453 General CN General C₂H₅OGeneral H H CH₃ H formula (112) formula (112) formula (112) 454 GeneralCN General C₂H₅O General H H CH₃O H formula (112) formula (112) formula(112) 455 General CN General C₂H₅O General H H t-C₄H₉ H formula (112)formula (112) formula (112) 456 General CN General C₂H₅O General H H ClH formula (112) formula (112) formula (112) 457 General CN General C₂H₅OGeneral H H F H formula (112) formula (112) formula (112) 458 General CNGeneral C₆H₅O General H H H H formula (112) formula (112) formula (112)459 General CN General C₆H₅O General H H CH₃ H formula (112) formula(112) formula (112) 460 General CN General C₆H₅O General H H CH₃O Hformula (112) formula (112) formula (112) 461 General CN General C₆H₅OGeneral H H t-C₄H₉ H formula (112) formula (112) formula (112) 462General CN General C₆H₅O General H H Cl H formula (112) formula (112)formula (112) 463 General CN General C₆H₅O General H H F H formula (112)formula (112) formula (112) 464 General CN General Formula (121) GeneralH H H H formula (112) formula (112) formula (112) 465 General CN GeneralFormula (121) General H H CH₃ H formula (112) formula (112) formula(112) 466 General CN General Formula (121) General H H CH₃O H formula(112) formula (112) formula (112) 467 General CN General Formula (121)General H H t-C₄H₉ H formula (112) formula (112) formula (112) 468General CN General Formula (121) General H H Cl H formula (112) formula(112) formula (112) 469 General CN General Formula (121) General H H F Hformula (112) formula (112) formula (112) 470 General CN General Formula(122) General H H H H formula (112) formula (112) formula (112) 471General CN General Formula (122) General H H CH₃ H formula (112) formula(112) formula (112) 472 General CN General Formula (122) General H HCH₃O H formula (112) formula (112) formula (112) 473 General CN GeneralFormula (122) General H H t-C₄H₉ H formula (112) formula (112) formula(112) 474 General CN General Formula (122) General H H Cl H formula(112) formula (112) formula (112) 475 General CN General Formula (122)General H H F H formula (112) formula (112) formula (112) 476 General CNGeneral Formula (123) General H H H H formula (112) formula (112)formula (112) 477 General CN General Formula (123) General H H CH₃ Hformula (112) formula (112) formula (112) 478 General CN General Formula(123) General H H CH₃O H formula (112) formula (112) formula (112) 479General CN General Formula (123) General H H t-C₄H₉ H formula (112)formula (112) formula (112) 480 General CN General Formula (123) GeneralH H Cl H formula (112) formula (112) formula (112) 481 General CNGeneral Formula (123) General H H F H formula (112) formula (112)formula (112) 482 General CN General Formula (124) General H H H Hformula (112) formula (112) formula (112) 483 General CN General Formula(124) General H H CH₃ H formula (112) formula (112) formula (112) 484General CN General Formula (124) General H H CH₃O H formula (112)formula (112) formula (112) 485 General CN General Formula (124) GeneralH H t-C₄H₉ H formula (112) formula (112) formula (112) 486 General CNGeneral Formula (124) General H H Cl H formula (112) formula (112)formula (112) 487 General CN General Formula (124) General H H F Hformula (112) formula (112) formula (112)

TABLE 2-4 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 488 General CN GeneralGeneral General H C₆H₅ H H formula (112) formula (112) formula (112)formula (112) 489 General CN General General General H H C₆H₅ H formula(112) formula (112) formula (112) formula (112) 490 General CN GeneralGeneral H H C₆H₅ H H formula (112) formula (112) formula (112) 491General CN General General H H H C₆H₅ H formula (112) formula (112)formula (112) 492 General CN General H General H C₆H₅ H H formula (112)formula (112) formula (112) 493 General CN General H General H H C₆H₅ Hformula (112) formula (112) formula (112) 494 General CN H GeneralGeneral H C₆H₅ H H formula (112) formula (112) formula (112) 495 GeneralCN H General General H H C₆H₅ H formula (112) formula (112) formula(112) 496 H CN General General General H C₆H₅ H H formula (112) formula(112) formula (112) 497 H CN General General General H H C₆H₅ H formula(112) formula (112) formula (112) 498 General CN General H H H C₆H₅ H Hformula (112) formula (112) 499 General CN General H H H H C₆H₅ Hformula (112) formula (112)   500-1 General CN H General H H C₆H₅ H Hformula (112) formula (112)   500-2 General CN H General H H H C₆H₅ Hformula (112) formula (112)   500-3 H CN General General H H C₆H₅ H Hformula (112) formula (112)   500-4 H CN General General H H H C₆H₅ Hformula (112) formula (112)   500-5 General CN H H General H C₆H₅ H Hformula (112) formula (112)   500-6 General CN H H General H H C₆H₅ Hformula (112) formula (112)   500-7 H CN General H General H C₆H₅ H Hformula (112) formula (112)   500-8 H CN General H General H H C₆H₅ Hformula (112) formula (112)   500-9 H CN H General General H C₆H₅ H Hformula (112) formula (112)   500-10 H CN H General General H H C₆H₅ Hformula (112) formula (112)   500-11 General CN H H H H C₆H₅ H H formula(112)   500-12 General CN H H H H H C₆H₅ H formula (112)   500-13 H CNGeneral H H H C₆H₅ H H formula (112)   500-14 H CN General H H H H C₆H₅H formula (112)   500-15 H CN H General H H C₆H₅ H H formula (112)  500-16 H CN H General H H H C₆H₅ H formula (112)   500-17 General CNGeneral General F H H C₆H₅ H formula (112) formula (112) formula (112)  500-18 General CN General F General H H C₆H₅ H formula (112) formula(112) formula (112)   500-19 General CN F General General H H C₆H₅ Hformula (112) formula (112) formula (112)   500-20 F CN General GeneralGeneral H H C₆H₅ H formula (112) formula (112) formula (112)   500-21General CN General F F H H C₆H₅ H formula (112) formula (112)   500-22General CN F General F H H C₆H₅ H formula (112) formula (112)   500-23 FCN General General F H H C₆H₅ H formula (112) formula (112)   500-24General CN F F General H H C₆H₅ H formula (112) formula (112)   500-25 FCN General F General H H C₆H₅ H formula (112) formula (112)   500-26 FCN F General General H H C₆H₅ H formula (112) formula (112)   500-27General CN F F F H H C₆H₅ H formula (112)   500-28 F CN General F F H HC₆H₅ H formula (112)   500-29 F CN F General F H H C₆H₅ H formula (112)  500-30 General CN General General OH H H C₆H₅ H formula (112) formula(112) formula (112)   500-31 General CN General OH General H H C₆H₅ Hformula (112) formula (112) formula (112)   500-32 General CN OH GeneralGeneral H H C₆H₅ H formula (112) formula (112) formula (112)   500-33 OHCN General General General H H C₆H₅ H formula (112) formula (112)formula (112)   500-34 General CN General OH OH H H C₆H₅ H formula (112)formula (112)   500-35 General CN OH General OH H H C₆H₅ H formula (112)formula (112)   500-36 OH CN General General OH H H C₆H₅ H formula (112)formula (112)   500-37 General CN OH OH General H H C₆H₅ H formula (112)formula (112)   500-38 OH CN General OH General H H C₆H₅ H formula (112)formula (112)   500-39 OH CN OH General General H H C₆H₅ H formula (112)formula (112)   500-40 General CN OH OH OH H H C₆H₅ H formula (112)  500-41 OH CN General OH OH H H C₆H₅ H formula (112)   500-42 OH CN OHGeneral OH H H C₆H₅ H formula (112)   500-43 OH CN OH OH General H HC₆H₅ H formula (112)   500-44 General CN General Cl General H H C₆H₅ Hformula (112) formula (112) formula (112)   500-45 General CN General FGeneral H H C₆H₅ H formula (112) formula (112) formula (112)   500-46General CN General CH₃O General H H C₆H₅ H formula (112) formula (112)formula (112)   500-47 General CN General C₂H₅O General H H C₆H₅ Hformula (112) formula (112) formula (112)   500-48 General CN GeneralC₆H₅O General H H C₆H₅ H formula (112) formula (112) formula (112)  500-49 General CN General Formula (121) General H H C₆H₅ H formula(112) formula (112) formula (112)   500-50 General CN General Formula(122) General H H C₆H₅ H formula (112) formula (112) formula (112)  500-51 General CN General Formula (123) General H H C₆H₅ H formula(112) formula (112) formula (112)   500-52 General CN General Formula(124) General H H C₆H₅ H formula (112) formula (112) formula (112)

TABLE 3-1 Compound General formula (1) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 501 CN General GeneralGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 502 CN General General General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 503 CN General GeneralGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 504 CN General General General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 505 CN General GeneralGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 506 CN General General General General H H t-C₄H₉ Hformula (112) formula (112) formula (112) formula (112) 507 CN GeneralGeneral General General H H Cl H formula (112) formula (112) formula(112) formula (112) 508 CN General General General General H H F Hformula (112) formula (112) formula (112) formula (112) 509 CN GeneralGeneral General General H H H CH₃ formula (112) formula (112) formula(112) formula (112) 510 CN General General General General H H H CH₃Oformula (112) formula (112) formula (112) formula (112) 511 CN GeneralGeneral General H H H H H formula (112) formula (112) formula (112) 512CN General General General H H H CH₃ H formula (112) formula (112)formula (112) 513 CN General General General H H H CH₃O H formula (112)formula (112) formula (112) 514 CN General General H General H H H Hformula (112) formula (112) formula (112) 515 CN General General HGeneral H H CH₃ H formula (112) formula (112) formula (112) 516 CNGeneral General H General H H CH₃O H formula (112) formula (112) formula(112) 517 CN General General H H H H H H formula (112) formula (112) 518CN General General H H H H CH₃ H formula (112) formula (112) 519 CNGeneral General H H H H CH₃O H formula (112) formula (112) 520 CNGeneral H General H H H H H formula (112) formula (112) 521 CN General HGeneral H H H CH₃ H formula (112) formula (112) 522 CN General H GeneralH H H CH₃O H formula (112) formula (112) 523 CN H General General H H HH H formula (112) formula (112) 524 CN H General General H H H CH₃ Hformula (112) formula (112) 525 CN H General General H H H CH₃O Hformula (112) formula (112) 526 CN General H H General H H H H formula(112) formula (112) 527 CN General H H General H H CH₃ H formula (112)formula (112) 528 CN General H H General H H CH₃O H formula (112)formula (112) 529 CN General H H H H H H H formula (112) 530 CN GeneralH H H H H CH₃ H formula (112) 531 CN General H H H H H CH₃O H formula(112) 532 CN H General H H H H H H formula (112) 533 CN H General H H HH CH₃ H formula (112) 534 CN H General H H H H CH₃O H formula (112) 535CN General General General F H H H H formula (112) formula (112) formula(112) 536 CN General General General F H H CH₃ H formula (112) formula(112) formula (112) 537 CN General General General F H H CH₃O H formula(112) formula (112) formula (112) 538 CN General General F General H H HH formula (112) formula (112) formula (112) 539 CN General General FGeneral H H CH₃ H formula (112) formula (112) formula (112) 540 CNGeneral General F General H H CH₃O H formula (112) formula (112) formula(112) 541 CN General General F F H H H H formula (112) formula (112) 542CN General General F F H H CH₃ H formula (112) formula (112) 543 CNGeneral General F F H H CH₃O H formula (112) formula (112) 544 CNGeneral F General F H H H H formula (112) formula (112) 545 CN General FGeneral F H H CH₃ H formula (112) formula (112) 546 CN General F GeneralF H H CH₃O H formula (112) formula (112) 547 CN F General General F H HH H formula (112) formula (112) 548 CN F General General F H H CH₃ Hformula (112) formula (112) 549 CN F General General F H H CH₃O Hformula (112) formula (112) 550 CN General F F General H H H H formula(112) formula (112) 551 CN General F F General H H CH₃ H formula (112)formula (112) 552 CN General F F General H H CH₃O H formula (112)formula (112) 553 CN General F F F H H H H formula (112) 554 CN GeneralF F F H H CH₃ H formula (112) 555 CN General F F F H H CH₃O H formula(112) 556 CN F General F F H H H H formula (112) 557 CN F General F F HH CH₃ H formula (112) 558 CN F General F F H H CH₃O H formula (112)

TABLE 3-2 General formula (1) General formula (112) Compound No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 559 CN General GeneralGeneral OH H H H H formula (112) formula (112) formula (112) 560 CNGeneral General General OH H H CH₃ H formula (112) formula (112) formula(112) 561 CN General General General OH H H CH₃O H formula (112) formula(112) formula (112) 562 CN General General OH General H H H H formula(112) formula (112) formula (112) 563 CN General General OH General H HCH₃ H formula (112) formula (112) formula (112) 654 CN General GeneralOH General H H CH₃O H formula (112) formula (112) formula (112) 565 CNGeneral General OH General H H Cl H formula (112) formula (112) formula(112) 566 CN General General OH General H H F H formula (112) formula(112) formula (112) 567 CN General General OH OH H H H H formula (112)formula (112) 568 CN General General OH OH H H CH₃ H formula (112)formula (112) 569 CN General General OH OH H H CH₃O H formula (112)formula (112) 570 CN General OH General OH H H H H formula (112) formula(112) 571 CN General OH General OH H H CH₃ H formula (112) formula (112)572 CN General OH General OH H H CH₃O H formula (112) formula (112) 573CN OH General General OH H H H H formula (112) formula (112) 574 CN OHGeneral General OH H H CH₃ H formula (112) formula (112) 575 CN OHGeneral General OH H H CH₃O H formula (112) formula (112) 576 CN GeneralOH OH General H H H H formula (112) formula (112) 577 CN General OH OHGeneral H H CH₃ H formula (112) formula (112) 578 CN General OH OHGeneral H H CH₃O H formula (112) formula (112) 579 CN General OH OH OH HH H H formula (112) 580 CN General OH OH OH H H CH₃ H formula (112) 581CN General OH OH OH H H CH₃O H formula (112) 582 CN OH General OH OH H HH H formula (112) 583 CN OH General OH OH H H CH₃ H formula (112) 584 CNOH General OH OH H H CH₃O H formula (112) 585 CN General General ClGeneral H H H H formula (112) formula (112) formula (112) 586 CN GeneralGeneral Cl General H H CH₃ H formula (112) formula (112) formula (112)587 CN General General Cl General H H CH₃O H formula (112) formula (112)formula (112) 588 CN General General Cl General H H t-C₄H₉ H formula(112) formula (112) formula (112) 589 CN General General Cl General H HCl H formula (112) formula (112) formula (112) 590 CN General General ClGeneral H H F H formula (112) formula (112) formula (112) 591 CN GeneralGeneral F General H H H H formula (112) formula (112) formula (112) 592CN General General F General H H CH₃ H formula (112) formula (112)formula (112) 593 CN General General F General H H CH₃O H formula (112)formula (112) formula (112) 594 CN General General F General H H t-C₄H₉H formula (112) formula (112) formula (112) 595 CN General General FGeneral H H Cl H formula (112) formula (112) formula (112) 596 CNGeneral General F General H H F H formula (112) formula (112) formula(112) 597 CN General General CH₃O General H H H H formula (112) formula(112) formula (112) 598 CN General General CH₃O General H H CH₃ Hformula (112) formula (112) formula (112) 599 CN General General CH₃OGeneral H H CH₃O H formula (112) formula (112) formula (112) 600 CNGeneral General CH₃O General H H t-C₄H₉ H formula (112) formula (112)formula (112) 601 CN General General CH₃O General H H Cl H formula (112)formula (112) formula (112) 602 CN General General CH₃O General H H F Hformula (112) formula (112) formula (112) 603 CN General General C₂H₅OGeneral H H H H formula (112) formula (112) formula (112) 604 CN GeneralGeneral C₂H₅O General H H CH₃ H formula (112) formula (112) formula(112) 605 CN General General C₂H₅O General H H CH₃O H formula (112)formula (112) formula (112) 606 CN General General C₂H₅O General H Ht-C₄H₉ H formula (112) formula (112) formula (112) 607 CN GeneralGeneral C₂H₅O General H H Cl H formula (112) formula (112) formula (112)608 CN General General C₂H₅O General H H F H formula (112) formula (112)formula (112) 609 CN General General C₆H₅O General H H H H formula (112)formula (112) formula (112) 610 CN General General C₆H₅O General H H CH₃H formula (112) formula (112) formula (112) 611 CN General General C₆H₅OGeneral H H CH₃O H formula (112) formula (112) formula (112) 612 CNGeneral General C₆H₅O General H H t-C₄H₉ H formula (112) formula (112)formula (112) 613 CN General General C₆H₅O General H H Cl H formula(112) formula (112) formula (112) 614 CN General General C₆H₅O General HH F H formula (112) formula (112) formula (112) 615 CN General Generalformula (121) General H H H H formula (112) formula (112) formula (112)616 CN General General formula (121) General H H CH₃ H formula (112)formula (112) formula (112) 617 CN General General formula (121) GeneralH H CH₃O H formula (112) formula (112) formula (112) 618 CN GeneralGeneral formula (121) General H H t-C₄H₉ H formula (112) formula (112)formula (112) 619 CN General General formula (121) General H H Cl Hformula (112) formula (112) formula (112) 620 CN General General formula(121) General H H F H formula (112) formula (112) formula (112)

TABLE 3-3 General formula (1) General formula (112) Compound No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 621 CN General Generalformula (122) General H H H H formula (112) formula (112) formula (112)622 CN General General formula (122) General H H CH₃ H formula (112)formula (112) formula (112) 623 CN General General formula (122) GeneralH H CH₃O H formula (112) formula (112) formula (112) 624 CN GeneralGeneral formula (122) General H H t-C₄H₉ H formula (112) formula (112)formula (112) 625 CN General General formula (122) General H H Cl Hformula (112) formula (112) formula (112) 626 CN General General formula(122) General H H F H formula (112) formula (112) formula (112) 627 CNGeneral General formula (123) General H H H H formula (112) formula(112) formula (112) 628 CN General General formula (123) General H H CH₃H formula (112) formula (112) formula (112) 629 CN General Generalformula (123) General H H CH₃O H formula (112) formula (112) formula(112) 630 CN General General formula (123) General H H t-C₄H₉ H formula(112) formula (112) formula (112) 631 CN General General formula (123)General H H Cl H formula (112) formula (112) formula (112) 632 CNGeneral General formula (123) General H H F H formula (112) formula(112) formula (112) 633 CN General General formula (124) General H H H Hformula (112) formula (112) formula (112) 634 CN General General formula(124) General H H CH₃ H formula (112) formula (112) formula (112) 635 CNGeneral General formula (124) General H H CH₃O H formula (112) formula(112) formula (112) 636 CN General General Formula (124) General H Ht-C₄H₉ H formula (112) formula (112) formula (112) 637 CN GeneralGeneral Formula (124) General H H Cl H formula (112) formula (112)formula (112) 638 CN General General Formula (124) General H H F Hformula (112) formula (112) formula (112) 639 CN General General GeneralGeneral H C₆H₅ H H formula (112) formula (112) formula (112) formula(112) 640 CN General General General General H H C₆H₅ H formula (112)formula (112) formula (112) formula (112) 641 CN General General GeneralH H C₆H₅ H H formula (112) formula (112) formula (112) 642 CN GeneralGeneral General H H H C₆H₅ H formula (112) formula (112) formula (112)643 CN General General H General H C₆H₅ H H formula (112) formula (112)formula (112) 644 CN General General H General H H C₆H₅ H formula (112)formula (112) formula (112) 645 CN General General H H H C₆H₅ H Hformula (112) formula (112) 646 CN General General H H H H C₆H₅ Hformula (112) formula (112) 647 CN General H General H H C₆H₅ H Hformula (112) formula (112) 648 CN General H General H H H C₆H₅ Hformula (112) formula (112) 649 CN H General General H H C₆H₅ H Hformula (112) formula (112) 650 CN H General General H H H C₆H₅ Hformula (112) formula (112) 651 CN H H General General H C₆H₅ H Hformula (112) formula (112) 652 CN H H General General H H C₆H₅ Hformula (112) formula (112) 653 CN General H H H H C₆H₅ H H formula(112) 654 CN General H H H H H C₆H₅ H formula (112) 655 CN H General H HH C₆H₅ H H formula (112) 656 CN H General H H H H C₆H₅ H formula (112)657 CN General General General F H H C₆H₅ H formula (112) formula (112)formula (112) 658 CN General General F General H H C₆H₅ H formula (112)formula (112) formula (112) 659 CN General General F F H H C₆H₅ Hformula (112) formula (112) 660 CN General F General F H H C₆H₅ Hformula (112) formula (112) 661 CN F General General F H H C₆H₅ Hformula (112) formula (112) 662 CN F F General General H H C₆H₅ Hformula (112) formula (112) 663 CN General F F F H H C₆H₅ H formula(112) 664 CN F General F F H H C₆H₅ H formula (112) 665 CN GeneralGeneral General OH H H C₆H₅ H formula (112) formula (112) formula (112)666 CN General General OH General H H C₆H₅ H formula (112) formula (112)formula (112) 667 CN General General OH OH H H C₆H₅ H formula (112)formula (112) 668 CN General OH General OH H H C₆H₅ H formula (112)formula (112) 669 CN OH General General OH H H C₆H₅ H formula (112)formula (112) 670 CN OH OH General General H H C₆H₅ H formula (112)formula (112) 671 CN General OH OH OH H H C₆H₅ H formula (112) 672 CN OHGeneral OH OH H H C₆H₅ H formula (112) 673 CN General General Cl GeneralH H C₆H₅ H formula (112) formula (112) formula (112) 674 CN GeneralGeneral F General H H C₆H₅ H formula (112) formula (112) formula (112)675 CN General General CH₃O General H H C₆H₅ H formula (112) formula(112) formula (112) 676 CN General General C₂H₅O General H H C₆H₅ Hformula (112) formula (112) formula (112) 677 CN General General C₆H₅OGeneral H H C₆H₅ H formula (112) formula (112) formula (112) 678 CNGeneral General Formula (121) General H H C₆H₅ H formula (112) formula(112) formula (112) 679 CN General General Formula (122) General H HC₆H₅ H formula (112) formula (112) formula (112) 680 CN General GeneralFormula (123) General H H C₆H₅ H formula (112) formula (112) formula(112) 681 CN General General Formula (124) General H H C₆H₅ H formula(112) formula (112) formula (112)

TABLE 4-1 General formula Compound General formula (1) (113) No. R¹ R²R³ R⁴ R⁵ R⁴¹ R⁴² 701 General General CN General General H H formula(113) formula (113) formula (113) formula (113) 702 General General CNGeneral General H CH₃ formula (113) formula (113) formula (113) formula(113) 703 General General CN General General H CH₃O formula (113)formula (113) formula (113) formula (113) 704 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 705General General CN General General H H formula (113) formula (113)formula (113) formula (113) 706 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 707 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 708 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 709 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 710General General CN General General H H formula (113) formula (113)formula (113) formula (113) 711 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 712 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 713 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 714 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 715General General CN General General H H formula (113) formula (113)formula (113) formula (113) 716 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 717 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 718 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 719 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 720General General CN General General H H formula (113) formula (113)formula (113) formula (113) 721 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 722 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 723 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 724 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 725General General CN General General H H formula (113) formula (113)formula (113) formula (113) 726 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 727 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 728 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 729 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 730General General CN General General H H formula (113) formula (113)formula (113) formula (113) 731 General General CN General General H Hformula (113) formula (113) formula (113) formula (113) 732 GeneralGeneral CN General General H H formula (113) formula (113) formula (113)formula (113) 733 General General CN General General H H formula (113)formula (113) formula (113) formula (113) 734 General General CN GeneralGeneral H H formula (113) formula (113) formula (113) formula (113) 735General General CN General H H H formula (113) formula (113) formula(113) 736 General General CN H General H H formula (113) formula (113)formula (113) 737 General General CN H H H H formula (113) formula (113)738 General H CN General H H H formula (113) formula (113) 739 H GeneralCN General H H H formula (113) formula (113) 740 General H CN H H H Hformula (113) 741 General General CN General F H H formula (113) formula(113) formula (113) 742 General General CN F General H H formula (113)formula (113) formula (113) 743 General General CN F F H H formula (113)formula (113) 744 General F CN General F H H formula (113) formula (113)745 F General CN General F H H formula (113) formula (113) 746 General FCN F F H H formula (113) 747 General General CN General OH H H formula(113) formula (113) formula (113) 748 General General CN OH General H Hformula (113) formula (113) formula (113) 749 General General CN OH OH HH formula (113) formula (113) 750 General OH CN General OH H H formula(113) formula (113) 751 OH General CN General OH H H formula (113)formula (113) 752 General OH CN OH OH H H formula (113) 753 GeneralGeneral CN Cl General H H formula (113) formula (113) formula (113) 754General General CN Cl General H H formula (113) formula (113) formula(113) 755 General General CN Cl General H H formula (113) formula (113)formula (113) 756 General General CN Cl General H H formula (113)formula (113) formula (113) 757 General General CN Cl General H Hformula (113) formula (113) formula (113) 758 General General CN ClGeneral H H formula (113) formula (113) formula (113) 759 GeneralGeneral CN F General H H formula (113) formula (113) formula (113) 760General General CN F General H H formula (113) formula (113) formula(113) 761 General General CN F General H H formula (113) formula (113)formula (113) 762 General General CN F General H H formula (113) formula(113) formula (113) 763 General General CN F General H H formula (113)formula (113) formula (113) 764 General General CN F General H H formula(113) formula (113) formula (113) 765 General General CN CH₃O General HH formula (113) formula (113) formula (113) Compound General formula(113) No. R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 701 H H H H 702 H H H H 703 H H H H 704 CH₃ HH H 705 CH₃O H H H 706 t-C₄H₉ H H H 707 Cl H H H 708 F H H H 709 H CH₃ HH 710 H CH₃O H H 711 H H CH₃ H 712 H H CH₃O H 713 H H t-C₄H₉ H 714 H HCl H 715 H H F H 716 H H C₆H₅ H 717 H H p-CH₃C₆H₄ H 718 H H2,4,6-(CH₃)₃C₆H₂ H 719 H H p-CH₃OC₆H₄ H 720 H H p-(CH₃)₂NC₆H₄ H 721 H Hp-FC₆H₄ H 722 H H p-CNC₆H₄ H 723 H H H CH₃ 724 H H H CH₃O 725 H H Ht-C₄H₉ 726 H H H Cl 727 H H H F 728 H H H C₆H₅ 729 H H H p-CH₃C₆H₄ 730 HH H 2,4,6-(CH₃)₃C₆H₂ 731 H H H p-CH₃OC₆H₄ 732 H H H p-(CH₃)₂NC₆H₄ 733 HH H p-FC₆H₄ 734 H H H p-CNC₆H₄ 735 H H H H 736 H H H H 737 H H H H 738 HH H H 739 H H H H 740 H H H H 741 H H H H 742 H H H H 743 H H H H 744 HH H H 745 H H H H 746 H H H H 747 H H H H 748 H H H H 749 H H H H 750 HH H H 751 H H H H 752 H H H H 753 H H H H 754 CH₃ H H H 755 CH₃O H H H756 t-C₄H₈ H H H 757 Cl H H H 758 F H H H 759 H H H H 760 CH₃ H H H 761CH₃O H H H 762 t-C₄H₈ H H H 763 Cl H H H 764 F H H H 765 H H H H

TABLE 4-2 Compound General formula (1) General formula (113) No. R¹ R²R³ R⁴ R⁵ R⁴¹ R⁴² R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 766 General General CN CH₃O General H HCH₃ H H H formula (113) formula (113) formula (113) 767 General GeneralCN CH₃O General H H CH₃O H H H formula (113) formula (113) formula (113)768 General General CN CH₃O General H H t-C₄H₈ H H H formula (113)formula (113) formula (113) 769 General General CN CH₃O General H H Cl HH H formula (113) formula (113) formula (113) 770 General General CNCH₃O General H H F H H H formula (113) formula (113) formula (113) 771General General CN C₂H₅O General H H H H H H formula (113) formula (113)formula (113) 772 General General CN C₂H₅O General H H CH₃ H H H formula(113) formula (113) formula (113) 773 General General CN C₂H₅O General HH CH₂O H H H formula (113) formula (113) formula (113) 774 GeneralGeneral CN C₂H₅O General H H t-C₄H₈ H H H formula (113) formula (113)formula (113) 775 General General CN C₂H₅O General H H Cl H H H formula(113) formula (113) formula (113) 776 General General CN C₂H₅O General HH F H H H formula (113) formula (113) formula (113) 777 General GeneralCN C₆H₅O General H H H H H H formula (113) formula (113) formula (113)778 General General CN C₆H₅O General H H CH₃ H H H formula (113) formula(113) formula (113) 779 General General CN C₆H₅O General H H CH₃O H H Hformula (113) formula (113) formula (113) 780 General General CN C₆H₅OGeneral H H t-C₄H₉ H H H formula (113) formula (113) formula (113) 781General General CN C₆H₅O General H H Cl H H H formula (113) formula(113) formula (113) 782 General General CN C₆H₅O General H H F H H Hformula (113) formula (113) formula (113) 783 General General CN Formula(121) General H H H H H H formula (113) formula (113) formula (113) 784General General CN Formula (121) General H H CH₃ H H H formula (113)formula (113) formula (113) 785 General General CN Formula (121) GeneralH H CH₃O H H H formula (113) formula (113) formula (113) 786 GeneralGeneral CN Formula (121) General H H t-C₄H₉ H H H formula (113) formula(113) formula (113) 787 General General CN Formula (121) General H H ClH H H formula (113) formula (113) formula (113) 788 General General CNFormula (121) General H H F H H H formula (113) formula (113) formula(113) 789 General General CN Formula (122) General H H H H H H formula(113) formula (113) formula (113) 790 General General CN Formula (122)General H H CH₃ H H H formula (113) formula (113) formula (113) 791General General CN Formula (122) General H H CH₃O H H H formula (113)formula (113) formula (113) 792 General General CN Formula (122) GeneralH H t-C₄H₉ H H H formula (113) formula (113) formula (113) 793 GeneralGeneral CN Formula (122) General H H Cl H H H formula (113) formula(113) formula (113) 794 General General CN Formula (122) General H H F HH H formula (113) formula (113) formula (113) 795 General General CNFormula (123) General H H H H H H formula (113) formula (113) formula(113) 796 General General CN Formula (123) General H H CH₃ H H H formula(113) formula (113) formula (113) 797 General General CN Formula (123)General H H CH₃O H H H formula (113) formula (113) formula (113) 798General General CN Formula (123) General H H t-C₄H₉ H H H formula (113)formula (113) formula (113) 799 General General CN Formula (123) GeneralH H Cl H H H formula (113) formula (113) formula (113) 800 GeneralGeneral CN Formula (123) General H H F H H H formula (113) formula (113)formula (113) 801 General General CN Formula (124) General H H H H H Hformula (113) formula (113) formula (113) 802 General General CN Formula(124) General H H CH₃ H H H formula (113) formula (113) formula (113)803 General General CN Formula (124) General H H CH₃O H H H formula(113) formula (113) formula (113) 804 General General CN Formula (124)General H H t-C₄H₉ H H H formula (113) formula (113) formula (113) 805General General CN Formula (124) General H H Cl H H H formula (113)formula (113) formula (113) 806 General General CN Formula (124) GeneralH H F H H H formula (113) formula (113) formula (113)

TABLE 5-1 General Compound General formula (1) formula (114) No. R¹ R²R³ R⁴ R⁵ R⁵² R⁵³ 901 General General CN General General H H formula(114) formula (114) formula (114) formula (114) 902 General General CNGeneral General CH₃ H formula (114) formula (114) formula (114) formula(114) 903 General General CN General General CH₃O H formula (114)formula (114) formula (114) formula (114) 904 General General CN GeneralGeneral H CH₃ formula (114) formula (114) formula (114) formula (114)905 General General CN General General H CH₃O formula (114) formula(114) formula (114) formula (114) 906 General General CN General GeneralH t-C₄H₉ formula (114) formula (114) formula (114) formula (114) 907General General CN General General H Cl formula (114) formula (114)formula (114) formula (114) 908 General General CN General General H Fformula (114) formula (114) formula (114) formula (114) 909 GeneralGeneral CN General General H H formula (114) formula (114) formula (114)formula (114) 910 General General CN General General H H formula (114)formula (114) formula (114) formula (114) 911 General General CN GeneralGeneral H H formula (114) formula (114) formula (114) formula (114) 912General General CN General General H H formula (114) formula (114)formula (114) formula (114) 913 General General CN General General H Hformula (114) formula (114) formula (114) formula (114) 914 GeneralGeneral CN General General H H formula (114) formula (114) formula (114)formula (114) 915 General General CN General General H H formula (114)formula (114) formula (114) formula (114) 916 General General CN GeneralGeneral H H formula (114) formula (114) formula (114) formula (114) 917General General CN General General H H formula (114) formula (114)formula (114) formula (114) 918 General General CN General General H Hformula (114) formula (114) formula (114) formula (114) 919 GeneralGeneral CN General H H H formula (114) formula (114) formula (114) 920General General CN H General H H formula (114) formula (114) formula(114) 921 General General CN H H H H formula (114) formula (114) 922General H CN General H H H formula (114) formula (114) 923 H General CNGeneral H H H formula (114) formula (114) 924 General H CN H H H Hformula (114) 925 General General CN General F H H formula (114) formula(114) formula (114) 926 General General CN F General H H formula (114)formula (114) formula (114) 927 General General CN F F H H formula (114)formula (114) 928 General F CN General F H H formula (114) formula (114)929 F General CN General F H H formula (114) formula (114) 930 General FCN F F H H formula (114) 931 General General CN General OH H H formula(114) formula (114) formula (114) 932 General General CN OH General H Hformula (114) formula (114) formula (114) 933 General General CN OH OH HH formula (114) formula (114) 934 General OH CN General OH H H formula(114) formula (114) 935 OH General CN General OH H H formula (114)formula (114) 936 General OH CN OH OH H H formula (114) 937 GeneralGeneral CN Cl General H H formula (114) formula (114) formula (114) 938General General CN Cl General H CH₃ formula (114) formula (114) formula(114) 939 General General CN Cl General H CH₃O formula (114) formula(114) formula (114) 940 General General CN Cl General H t-C₄H₉ formula(114) formula (114) formula (114) 941 General General CN Cl General H Clformula (114) formula (114) formula (114) 942 General General CN ClGeneral H F formula (114) formula (114) formula (114) 943 GeneralGeneral CN F General H H formula (114) formula (114) formula (114) 944General General CN F General H CH₃ formula (114) formula (114) formula(114) 945 General General CN F General H CH₃O formula (114) formula(114) formula (114) 946 General General CN F General H t-C₄H₉ formula(114) formula (114) formula (114) 947 General General CN F General H Clformula (114) formula (114) formula (114) 948 General General CN FGeneral H F formula (114) formula (114) formula (114) 949 GeneralGeneral CN CH₃O General H H formula (114) formula (114) formula (114)950 General General CN CH₃O General H CH₃ formula (114) formula (114)formula (114) 951 General General CN CH₃O General H CH₃O formula (114)formula (114) formula (114) 952 General General CN CH₃O General H t-C₄H₉formula (114) formula (114) formula (114) 953 General General CN CH₃OGeneral H Cl formula (114) formula (114) formula (114) 954 GeneralGeneral CN CH₃O General H F formula (114) formula (114) formula (114)955 General General CN C₂H₅O General H H formula (114) formula (114)formula (114) 956 General General CN C₂H₅O General H CH₃ formula (114)formula (114) formula (114) 957 General General CN C₂H₅O General H CH₃Oformula (114) formula (114) formula (114) 958 General General CN C₂H₅OGeneral H t-C₄H₉ formula (114) formula (114) formula (114) 959 GeneralGeneral CN C₂H₅O General H Cl formula (114) formula (114) formula (114)960 General General CN C₂H₅O General H F formula (114) formula (114)formula (114) 961 General General CN C₆H₅ O General H H formula (114)formula (114) formula (114) 962 General General CN C₆H₅ O General H CH₃formula (114) formula (114) formula (114) 963 General General CN C₆H₅ OGeneral H CH₃O formula (114) formula (114) formula (114) 964 GeneralGeneral CN C₆H₅ O General H t-C₄H₉ formula (114) formula (114) formula(114) 965 General General CN C₆H₅ O General H Cl formula (114) formula(114) formula (114) General formula (114) R⁵¹, R⁵⁶, Compound R⁵⁸, R⁶⁰,No. R⁵⁴ R⁵⁶ R⁵⁷ R⁵⁸ R⁶¹ R⁶² 901 H H H H H H 902 H H H H H H 903 H H H HH H 904 H H H H H H 905 H H H H H H 906 H H H H H H 907 H H H H H H 908H H H H H H 909 CH₃ H H H H H 910 CH₃O H H H H H 911 H CH₃ H H H H 912 HCH₃O H H H H 913 H H CH₃ H H H 914 H H CH₃O H H H 915 H H H CH₃ H H 916H H H CH₃O H H 917 H H H H CH₃ H 918 H H H H CH₃O H 919 H H H H H H 920H H H H H H 921 H H H H H H 922 H H H H H H 923 H H H H H H 924 H H H HH H 925 H H H H H H 926 H H H H H H 927 H H H H H H 928 H H H H H H 929H H H H H H 930 H H H H H H 931 H H H H H H 932 H H H H H H 933 H H H HH H 934 H H H H H H 935 H H H H H H 936 H H H H H H 937 H H H H H H 938H H H H H H 939 H H H H H H 940 H H H H H H 941 H H H H H H 942 H H H HH H 943 H H H H H H 944 H H H H H H 945 H H H H H H 946 H H H H H H 947H H H H H H 948 H H H H H H 949 H H H H H H 950 H H H H H H 951 H H H HH H 952 H H H H H H 953 H H H H H H 954 H H H H H H 955 H H H H H H 956H H H H H H 957 H H H H H H 958 H H H H H H 959 H H H H H H 960 H H H HH H 961 H H H H H H 962 H H H H H H 963 H H H H H H 964 H H H H H H 965H H H H H H

TABLE 5-2 General formula (114) R⁵¹, R⁵⁶, Compound General formula (1)R⁵⁸, R⁶⁰, No. R¹ R² R³ R⁴ R⁵ R⁵² R⁵³ R⁵⁴ R⁵⁶ R⁵⁷ R⁵⁸ R⁶¹ R⁶² 966 GeneralGeneral CN C₆H₅ O General H F H H H H H H formula (114) formula (114)formula (114) 967 General General CN Formula (121) General H H H H H H HH formula (114) formula (114) formula (114) 968 General General CNFormula (121) General H CH₃ H H H H H H formula (114) formula (114)formula (114) 969 General General CN Formula (121) General H CH₃O H H HH H H formula (114) formula (114) formula (114) 970 General General CNFormula (121) General H t-C₄H₉ H H H H H H formula (114) formula (114)formula (114) 971 General General CN Formula (121) General H Cl H H H HH H formula (114) formula (114) formula (114) 972 General General CNFormula (121) General H F H H H H H H formula (114) formula (114)formula (114) 973 General General CN Formula (122) General H H H H H H HH formula (114) formula (114) formula (114) 974 General General CNFormula (122) General H CH₃ H H H H H H formula (114) formula (114)formula (114) 975 General General CN Formula (122) General H CH₃O H H HH H H formula (114) formula (114) formula (114) 976 General General CNFormula (122) General H t-C₄H₉ H H H H H H formula (114) formula (114)formula (114) 977 General General CN Formula (122) General H Cl H H H HH H formula (114) formula (114) formula (114) 978 General General CNFormula (122) General H F H H H H H H formula (114) formula (114)formula (114) 989 General General CN Formula (123) General H H H H H H HH formula (114) formula (114) formula (114) 980 General General CNFormula (123) General H CH₃ H H H H H H formula (114) formula (114)formula (114) 981 General General CN Formula (123) General H CH₃O H H HH H H formula (114) formula (114) formula (114) 982 General General CNFormula (123) General H t-C₄H₉ H H H H H H formula (114) formula (114)formula (114) 983 General General CN Formula (123) General H Cl H H H HH H formula (114) formula (114) formula (114) 984 General General CNFormula (123) General H F H H H H H H formula (114) formula (114)formula (114) 985 General General CN Formula (124) General H H H H H H HH formula (114) formula (114) formula (114) 986 General General CNFormula (124) General H CH₃ H H H H H H formula (114) formula (114)formula (114) 987 General General CN Formula (124) General H CH₃O H H HH H H formula (114) formula (114) formula (114) 988 General General CNFormula (124) General H t-C₄H₉ H H H H H H formula (114) formula (114)formula (114) 989 General General CN Formula (124) General H Cl H H H HH H formula (114) formula (114) formula (114) 990 General General CNFormula (124) General H F H H H H H H formula (114) formula (114)formula (114)

TABLE 6-1 Compound General formula (1) General formula (115) No. R¹ R²R³ R⁴ R⁵ R⁷¹, R⁸⁰ R⁷², R⁷⁹ R⁷³, R⁷⁸ R⁷⁴, R⁷⁷ R⁷⁵, R⁷⁶ 1001 GeneralGeneral CN General General H H H H H formula (115) formula (115) formula(115) formula (115) 1002 General General CN General General H CH₃ H H Hformula (115) formula (115) formula (115) formula (115) 1003 GeneralGeneral CN General General H CH₃O H H H formula (115) formula (115)formula (115) formula (115) 1004 General General CN General General HC₆H₅ H H H formula (115) formula (115) formula (115) formula (115) 1005General General CN General General H CH₃ H CH₃ H formula (115) formula(115) formula (115) formula (115) 1006 General General CN GeneralGeneral H CH₃O H CH₃O H formula (115) formula (115) formula (115)formula (115) 1007 General General CN General General H C₆H₅ H C₆H₅ Hformula (115) formula (115) formula (115) formula (115) 1008 GeneralGeneral CN General General H H CH₃ H H formula (115) formula (115)formula (115) formula (115) 1009 General General CN General General H HCH₃O H H formula (115) formula (115) formula (115) formula (115) 1010General General CN General General H H t-C₄H₉ H H formula (115) formula(115) formula (115) formula (115) 1011 General General CN GeneralGeneral H H Cl H H formula (115) formula (115) formula (115) formula(115) 1012 General General CN General General H H F H H formula (115)formula (115) formula (115) formula (115) 1013 General General CNGeneral General H H C₆H₅ H H formula (115) formula (115) formula (115)formula (115) 1014 General General CN General General H H p-C₆H₅—C₆H₄ HH formula (115) formula (115) formula (115) formula (115) 1015 GeneralGeneral CN General H H H H H H formula (115) formula (115) formula (115)1016 General General CN H General H H H H H formula (115) formula (115)formula (115) 1017 General General CN H H H H H H H formula (115)formula (115) 1018 General H CN General H H H H H H formula (115)formula (115) 1019 H General CN General H H H H H H formula (115)formula (115) 1020 General H CN H H H H H H H formula (115) 1021 GeneralGeneral CN General F H H H H H formula (115) formula (115) formula (115)1022 General General CN F General H H H H H formula (115) formula (115)formula (115) 1023 General General CN F F H H H H H formula (115)formula (115) 1024 General F CN General F H H H H H formula (115)formula (115) 1025 F General CN General F H H H H H formula (115)formula (115) 1026 General F CN F F H H H H H formula (115) 1027 GeneralGeneral CN General OH H H H H H formula (115) formula (115) formula(115) 1028 General General CN OH General H H H H H formula (115) formula(115) formula (115) 1029 General General CN OH OH H H H H H formula(115) formula (115) 1030 General OH CN General OH H H H H H formula(115) formula (115) 1031 OH General CN General OH H H H H H formula(115) formula (115) 1032 General OH CN OH OH H H H H H formula (115)1033 General General CN Cl General H H H H H formula (115) formula (115)formula (115) 1034 General General CN Cl General H H CH₃ H H formula(115) formula (115) formula (115) 1035 General General CN Cl General H HCH₃O H H formula (115) formula (115) formula (115) 1036 General GeneralCN Cl General H H t-C₄H₉ H H formula (115) formula (115) formula (115)1037 General General CN Cl General H H Cl H H formula (115) formula(115) formula (115) 1038 General General CN Cl General H H F H H formula(115) formula (115) formula (115) 1039 General General CN F General H HH H H formula (115) formula (115) formula (115) 1040 General General CNF General H H CH₃ H H formula (115) formula (115) formula (115) 1041General General CN F General H H CH₃O H H formula (115) formula (115)formula (115) 1042 General General CN F General H H t-C₄H₉ H H formula(115) formula (115) formula (115) 1043 General General CN F General H HCl H H formula (115) formula (115) formula (115) 1044 General General CNF General H H F H H formula (115) formula (115) formula (115) 1045General General CN CH₃O General H H H H H formula (115) formula (115)formula (115) 1046 General General CN CH₃O General H H CH₃ H H formula(115) formula (115) formula (115) 1047 General General CN CH₃O General HH CH₃O H H formula (115) formula (115) formula (115) 1048 GeneralGeneral CN CH₃O General H H t-C₄H₉ H H formula (115) formula (115)formula (115) 1049 General General CN CH₃O General H H Cl H H formula(115) formula (115) formula (115) 1050 General General CN CH₃O General HH F H H formula (115) formula (115) formula (115) 1051 General GeneralCN C₂H₅O General H H H H H formula (115) formula (115) formula (115)1052 General General CN C₂H₅O General H H CH₃ H H formula (115) formula(115) formula (115) 1053 General General CN C₂H₅O General H H CH₃O H Hformula (115) formula (115) formula (115) 1054 General General CN C₂H₅OGeneral H H t-C₄H₉ H H formula (115) formula (115) formula (115) 1055General General CN C₂H₅O General H H Cl H H formula (115) formula (115)formula (115) 1056 General General CN C₂H₅O General H H F H H formula(115) formula (115) formula (115) 1057 General General CN C₆H₅ O GeneralH H H H H formula (115) formula (115) formula (115) 1058 General GeneralCN C₆H₅ O General H H CH₃ H H formula (115) formula (115) formula (115)1059 General General CN C₆H₅ O General H H CH₃O H H formula (115)formula (115) formula (115) 1060 General General CN C₆H₅ O General H Ht-C₄H₉ H H formula (115) formula (115) formula (115)

TABLE 6-2 Compound General formula (1) General formula (115) No. R¹ R²R³ R⁴ R⁵ R⁷¹, R⁸⁰ R⁷², R⁷⁹ R⁷³, R⁷⁸ R⁷⁴, R⁷⁷ R⁷⁵, R⁷⁶ 1061 GeneralGeneral CN C₆H₅O General H H Cl H H formula (115) formula (115) formula(115) 1062 General General CN C₆H₅O General H H F H H formula (115)formula (115) formula (115) 1063 General General CN Formula General H HH H H formula (115) formula (115) (121) formula (115) 1064 GeneralGeneral CN Formula General H H CH₃ H H formula (115) formula (115) (121)formula (115) 1065 General General CN Formula General H H CH₃O H Hformula (115) formula (115) (121) formula (115) 1066 General General CNFormula General H H t-C₄H₉ H H formula (115) formula (115) (121) formula(115) 1067 General General CN Formula General H H Cl H H formula (115)formula (115) (121) formula (115) 1068 General General CN FormulaGeneral H H F H H formula (115) formula (115) (121) formula (115) 1069General General CN Formula General H H H H H formula (115) formula (115)(122) formula (115) 1070 General General CN Formula General H H CH₃ H Hformula (115) formula (115) (122) formula (115) 1071 General General CNFormula General H H CH₃O H H formula (115) formula (115) (122) formula(115) 1072 General General CN Formula General H H t-C₄H₉ H H formula(115) formula (115) (122) formula (115) 1073 General General CN FormulaGeneral H H Cl H H formula (115) formula (115) (122) formula (115) 1074General General CN Formula General H H F H H formula (115) formula (115)(122) formula (115) 1075 General General CN Formula General H H H H Hformula (115) formula (115) (123) formula (115) 1076 General General CNFormula General H H CH₃ H H formula (115) formula (115) (123) formula(115) 1077 General General CN Formula General H H CH₃O H H formula (115)formula (115) (123) formula (115) 1078 General General CN FormulaGeneral H H t-C₄H₉ H H formula (115) formula (115) (123) formula (115)1079 General General CN Formula General H H Cl H H formula (115) formula(115) (123) formula (115) 1080 General General CN Formula General H H FH H formula (115) formula (115) (123) formula (115) 1081 General GeneralCN Formula General H H H H H formula (115) formula (115) (124) formula(115) 1082 General General CN Formula General H H CH₃ H H formula (115)formula (115) (124) formula (115) 1083 General General CN FormulaGeneral H H CH₃O H H formula (115) formula (115) (124) formula (115)1084 General General CN Formula General H H t-C₄H₉ H H formula (115)formula (115) (124) formula (115) 1085 General General CN FormulaGeneral H H Cl H H formula (115) formula (115) (124) formula (115) 1086General General CN Formula General H H F H H formula (115) formula (115)(124) formula (115)

Examples of the preferred light, emitting material capable of emittingdelayed fluorescent light include the following compounds.

(1) A compound represented by the following general formula (131):

wherein in the general formula (131), from 0 to 1 of R¹ to R⁵ representsa cyano group, from 1 to 5 of R¹ to R⁵ each represent a grouprepresented by the following general formula (132), and the balance ofR¹ to R⁵ each represent a hydrogen atom or a substituent other than theabove,

wherein in the general formula (132), R¹¹ to R²⁰ each independentlyrepresent a hydrogen atom or a substituent, provided that R¹¹ and R¹²,R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, R¹⁷ andR¹⁸, R¹⁸ and R¹⁹, and R¹⁹ and R²⁰ each may be bonded to each other toform a ring structure; and L¹² represents a substituted or unsubstitutedarylene group or a substituted or unsubstituted heteroarylene group.

(2) The compound according to the item (1), wherein the grouprepresented by the general formula (132) is a group represented by anyone of the following general formulae (133) to (138):

wherein in the general formulae (133) to (138), R²¹ to R²⁴, R²⁷ to R³⁸,R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁶, R⁶¹ to R⁶⁵, R⁷¹ to R⁷⁹, R⁸¹ to R⁹⁰ eachindependently represent a hydrogen atom or a substituent, provided thatR²¹ to R²², R²² to R²³, R²³ to R²⁴, R²⁷ and R²⁸, R²⁸ and R²⁹, R²⁹ andR³⁰, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷,R³⁷ and R³⁸, R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ andR⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶,R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ andR⁶⁵, R⁵⁴ and R⁶¹, R⁵⁵ and R⁶⁶, R⁷¹ and R⁶², R⁷² and R⁷³, R⁷³ and R⁷⁴,R⁷⁴ and R⁷⁵, R⁷⁶ and R⁷⁷, R⁷⁷ and R⁷⁸, R⁷⁸ and R⁷⁹, R⁸¹ and R⁸², R⁸² andR⁸³, R⁸³ and R⁸⁴, R⁸⁵ and R⁸⁶, R⁸⁶ and R⁸⁷, R⁸⁷ and R⁸⁸, and R⁸⁹ and R⁹⁰each may be bonded to each other to form a ring structure; and L¹³ toL¹⁸ each independently represent a substituted or unsubstituted arylenegroup or a substituted or unsubstituted heteroarylene group.

(3) The compound according to the item (1) or (2), wherein in thegeneral formula (131), R³ represents a cyano group.

(4) The compound according to any one of the items (1) to (3), whereinin the general formula (131), R¹ and R⁴ each represent a grouprepresented by the general formula (132).

(5) The compound according to any one of the items (1) to (4), whereinin the general formula (132), represents a phenylene group.

(6) The compound according to any one of the items (1) to (5), whereinthe group represented by the general formula (132) is a grouprepresented by the general formula (133).

(7) the compound according to the item (6), wherein in the generalformula (133), L¹³ represents a 1,3-phenylene group.

(8) The compound according to any one of the items (1) to (5), whereinthe group represented by the general formula (132) is a grouprepresented by the general formula (134).

(9) The compound according to the item (8), wherein in the generalformula (134), L¹⁴ represents a 1,4-phenylene group.

(10) The compound according to any one of the items (1) to (5), whereinthe group represented by the general formula (132) is a grouprepresented by the general formula (138).

(11) The compound according to the item (10), wherein in the generalformula (138), represents a 1,4-phenylene group.

Examples of the compound include the following compounds.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (141), The entire description of WO 2013/011954including the paragraphs 0007 to 0047 and 0073 to 0085 is incorporatedherein by reference.

wherein in the general formula (141), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ andR¹⁷ each independently represent a hydrogen atom or an electron donatinggroup, provided that at least one thereof represents an electrondonating group; R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ eachindependently represent a hydrogen atom or an electron withdrawing grouphaving no unshared electron pair at the α-position; and Z represents asingle bond or >C═Y, wherein Y represents O, S, C(CN)₂ or C(COOH)₂,provided that when Z represents a single bond, at least one of R⁹, R¹⁰,R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ represents an electron withdrawing grouphaving no unshared electron pair at the α-position.

Specific examples of the compounds include the compounds shown in thefollowing tables. In the tables, D1 to D3 represent the following arylgroups substituted by an electron donating group, respectively; A1 to A5represent the following electron withdrawing groups, respectively; Hrepresents a hydrogen atom; and Ph represents a phenyl group.

TABLE 7 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2001 H H A1 A1 Phsingle bond H 2002 H D1 A1 A1 Ph single bond H 2003 H D2 A1 A1 Ph singlebond H 2004 H D3 A1 A1 Ph single bond H 2005 H H A2 A2 Ph single bond H2006 H D1 A2 A2 Ph single bond H 2007 H D2 A2 A2 Ph single bond H 2008 HD3 A2 A2 Ph single bond H 2009 H H A3 A3 Ph single bond H 2010 H D1 A3A3 Ph single bond H 2011 H D2 A3 A3 Ph single bond H 2012 H D3 A3 A3 Phsingle bond H 2013 H H A4 A4 Ph single bond H 2014 H D1 A4 A4 Ph singlebond H 2015 H D2 A4 A4 Ph single bond H 2016 H D3 A4 A4 Ph single bond H2017 H H A5 A5 Ph single bond H 2018 H D1 A5 A5 Ph single bond H 2019 HD2 A5 A5 Ph single bond H 2020 H D3 A5 A5 Ph single bond H 2021 D1 D1 A1A1 Ph single bond H 2022 D2 D2 A1 A1 Ph single bond H 2023 D3 D3 A1 A1Ph single bond H 2024 D1 D1 A2 A2 Ph single bond H 2025 D2 D2 A2 A2 Phsingle bond H 2026 D3 D3 A2 A2 Ph single bond H 2027 D1 D1 A3 A3 Phsingle bond H 2028 D2 D2 A3 A3 Ph single bond H 2029 D3 D3 A3 A3 Phsingle bond H 2030 D1 D1 A4 A4 Ph single bond H 2031 D2 D2 A4 A4 Phsingle bond H 2032 D3 D3 A4 A4 Ph single bond H 2033 D1 D1 A5 A5 Phsingle bond H 2034 D2 D2 A5 A5 Ph single bond H 2035 D3 D3 A5 A5 Phsingle bond H

TABLE 8 Compound No. R² R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2036 H H H A1 Phsingle bond H 2037 H D1 H A1 Ph single bond H 2038 H D2 H A1 Ph singlebond H 2039 H D3 H A1 Ph single bond H 2040 H H H A2 Ph single bond H2041 H D1 H A2 Ph single bond H 2042 H D2 H A2 Ph single bond H 2043 HD3 H A2 Ph single bond H 2044 H H H A3 Ph single bond H 2045 H D1 H A3Ph single bond H 2046 H D2 H A3 Ph single bond H 2047 H D3 H A3 Phsingle bond H 2048 H H H A4 Ph single bond H 2049 H D1 H A4 Ph singlebond H 2050 H D2 H A4 Ph single bond H 2051 H D3 H A4 Ph single bond H2052 H H H A5 Ph single bond H 2053 H D1 H A5 Ph single bond H 2054 H D2H A5 Ph single bond H 2055 H D3 H A5 Ph single bond H 2056 D1 D1 H A1 Phsingle bond H 2057 D2 D2 H A1 Ph single bond H 2058 D3 D3 H A1 Ph singlebond H 2059 D1 D1 H A2 Ph single bond H 2060 D2 D2 H A2 Ph single bond H2061 D3 D3 H A2 Ph single bond H 2062 D1 D1 H A3 Ph single bond H 2063D2 D2 H A3 Ph single bond H 2064 D3 D3 H A3 Ph single bond H 2065 D1 D1H A4 Ph single bond H 2066 D2 D2 H A4 Ph single bond H 2067 D3 D3 H A4Ph single bond H 2068 D1 D1 H A5 Ph single bond H 2069 D2 D2 H A5 Phsingle bond H 2070 D3 D3 H A5 Ph single bond H

TABLE 9 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2071 H H A1 A1 Ph C═OH 2072 H D1 A1 A1 Ph C═O H 2073 H D2 A1 A1 Ph C═O H 2074 H D3 A1 A1 PhC═O H 2075 H H A2 A2 Ph C═O H 2076 H D1 A2 A2 Ph C═O H 2077 H D2 A2 A2Ph C═O H 2078 H D3 A2 A2 Ph C═O H 2079 H H A3 A3 Ph C═O H 2080 H D1 A3A3 Ph C═O H 2081 H D2 A3 A3 Ph C═O H 2082 H D3 A3 A3 Ph C═O H 2083 H HA4 A4 Ph C═O H 2084 H D1 A4 A4 Ph C═O H 2085 H D2 A4 A4 Ph C═O H 2086 HD3 A4 A4 Ph C═O H 2087 H H A5 A5 Ph C═O H 2088 H D1 A5 A5 Ph C═O H 2089H D2 A5 A5 Ph C═O H 2090 H D3 A5 A5 Ph C═O H 2091 D1 D1 A1 A1 Ph C═O H2092 D2 D2 A1 A1 Ph C═O H 2093 D3 D3 A1 A1 Ph C═O H 2094 D1 D1 A2 A2 PhC═O H 2095 D2 D2 A2 A2 Ph C═O H 2096 D3 D3 A2 A2 Ph C═O H 2097 D1 D1 A3A3 Ph C═O H 2098 D2 D2 A3 A3 Ph C═O H 2099 D3 D3 A3 A3 Ph C═O H 2100 D1D1 A4 A4 Ph C═O H 2101 D2 D2 A4 A4 Ph C═O H 2102 D3 D3 A4 A4 Ph C═O H2103 D1 D1 A5 A5 Ph C═O H 2104 D2 D2 A5 A5 Ph C═O H 2105 D3 D3 A5 A5 PhC═O H

TABLE 10 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2106 H H H A1 Ph C═OH 2107 H D1 H A1 Ph C═O H 2108 H D2 H A1 Ph C═O H 2109 H D3 H A1 Ph C═OH 2110 H H H A2 Ph C═O H 2111 H D1 H A2 Ph C═O H 2112 H D2 H A2 Ph C═O H2113 H D3 H A2 Ph C═O H 2114 H H H A3 Ph C═O H 2115 H D1 H A3 Ph C═O H2116 H D2 H A3 Ph C═O H 2117 H D3 H A3 Ph C═O H 2118 H H H A4 Ph C═O H2119 H D1 H A4 Ph C═O H 2120 H D2 H A4 Ph C═O H 2121 H D3 H A4 Ph C═O H2122 H H H A5 Ph C═O H 2123 H D1 H A5 Ph C═O H 2124 H D2 H A5 Ph C═O H2125 H D3 H A5 Ph C═O H 2126 D1 D1 H A1 Ph C═O H 2127 D2 D2 H A1 Ph C═OH 2128 D3 D3 H A1 Ph C═O H 2129 D1 D1 H A2 Ph C═O H 2130 D2 D2 H A2 PhC═O H 2131 D3 D3 H A2 Ph C═O H 2132 D1 D1 H A3 Ph C═O H 2133 D2 D2 H A3Ph C═O H 2134 D3 D3 H A3 Ph C═O H 2135 D1 D1 H A4 Ph C═O H 2136 D2 D2 HA4 Ph C═O H 2137 D3 D3 H A4 Ph C═O H 2138 D1 D1 H A5 Ph C═O H 2139 D2 D2H A5 Ph C═O H 2140 D3 D3 H A5 Ph C═O H 2141 H H H H Ph C═O H

TABLE 11 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2142 H H A1 A1 Ph C═SH 2143 H D1 A1 A1 Ph C═S H 2144 H D2 A1 A1 Ph C═S H 2145 H D3 A1 A1 PhC═S H 2146 H H A2 A2 Ph C═S H 2147 H D1 A2 A2 Ph C═S H 2148 H D2 A2 A2Ph C═S H 2149 H D3 A2 A2 Ph C═S H 2150 H H A3 A3 Ph C═S H 2151 H D1 A3A3 Ph C═S H 2152 H D2 A3 A3 Ph C═S H 2153 H D3 A3 A3 Ph C═S H 2154 H HA4 A4 Ph C═S H 2155 H D1 A4 A4 Ph C═S H 2156 H D2 A4 A4 Ph C═S H 2157 HD3 A4 A4 Ph C═S H 2158 H H A5 A5 Ph C═S H 2159 H D1 A5 A5 Ph C═S H 2160H D2 A5 A5 Ph C═S H 2161 H D3 A5 A5 Ph C═S H 2162 D1 D1 A1 A1 Ph C═S H2163 D2 D2 A1 A1 Ph C═S H 2164 D3 D3 A1 A1 Ph C═S H 2165 D1 D1 A2 A2 PhC═S H 2166 D2 D2 A2 A2 Ph C═S H 2167 D3 D3 A2 A2 Ph C═S H 2168 D1 D1 A3A3 Ph C═S H 2169 D2 D2 A3 A3 Ph C═S H 2170 D3 D3 A3 A3 Ph C═S H 2171 D1D1 A4 A4 Ph C═S H 2172 D2 D2 A4 A4 Ph C═S H 2173 D3 D3 A4 A4 Ph C═S H2174 D1 D1 A5 A5 Ph C═S H 2175 D2 D2 A5 A5 Ph C═S H 2176 D3 D3 A5 A5 PhC═S H

TABLE 12 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2177 H H H A1 Ph C═SH 2178 H D1 H A1 Ph C═S H 2179 H D2 H A1 Ph C═S H 2180 H D3 H A1 Ph C═SH 2181 H H H A2 Ph C═S H 2182 H D1 H A2 Ph C═S H 2183 H D2 H A2 Ph C═S H2184 H D3 H A2 Ph C═S H 2185 H H H A3 Ph C═S H 2186 H D1 H A3 Ph C═S H2187 H D2 H A3 Ph C═S H 2188 H D3 H A3 Ph C═S H 2189 H H H A4 Ph C═S H2190 H D1 H A4 Ph C═S H 2191 H D2 H A4 Ph C═S H 2192 H D3 H A4 Ph C═S H2193 H H H A5 Ph C═S H 2194 H D1 H A5 Ph C═S H 2195 H D2 H A5 Ph C═S H2196 H D3 H A5 Ph C═S H 2197 D1 D1 H A1 Ph C═S H 2198 D2 D2 H A1 Ph C═SH 2199 D3 D3 H A1 Ph C═S H 2200 D1 D1 H A2 Ph C═S H 2201 D2 D2 H A2 PhC═S H 2202 D3 D3 H A2 Ph C═S H 2203 D1 D1 H A3 Ph C═S H 2204 D2 D2 H A3Ph C═S H 2205 D3 D3 H A3 Ph C═S H 2206 D1 D1 H A4 Ph C═S H 2207 D2 D2 HA4 Ph C═S H 2208 D3 D3 H A4 Ph C═S H 2209 D1 D1 H A5 Ph C═S H 2210 D2 D2H A5 Ph C═S H 2211 D3 D3 H A5 Ph C═S H 2212 H H H H Ph C═S H

TABLE 13 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2213 H H A1 A1 PhC═C(CN)₂ H 2214 H D1 A1 A1 Ph C═C(CN)₂ H 2215 H D2 A1 A1 Ph C═C(CN)₂ H2216 H D3 A1 A1 Ph C═C(CN)₂ H 2217 H H A2 A2 Ph C═C(CN)₂ H 2218 H D1 A2A2 Ph C═C(CN)₂ H 2219 H D2 A2 A2 Ph C═C(CN)₂ H 2220 H D3 A2 A2 PhC═C(CN)₂ H 2221 H H A3 A3 Ph C═C(CN)₂ H 2222 H D1 A3 A3 Ph C═C(CN)₂ H2223 H D2 A3 A3 Ph C═C(CN)₂ H 2224 H D3 A3 A3 Ph C═C(CN)₂ H 2225 H H A4A4 Ph C═C(CN)₂ H 2226 H D1 A4 A4 Ph C═C(CN)₂ H 2227 H D2 A4 A4 PhC═C(CN)₂ H 2228 H D3 A4 A4 Ph C═C(CN)₂ H 2229 H H A5 A5 Ph C═C(CN)₂ H2230 H D1 A5 A5 Ph C═C(CN)₂ H 2231 H D2 A5 A5 Ph C═C(CN)₂ H 2232 H D3 A5A5 Ph C═C(CN)₂ H 2233 D1 D1 A1 A1 Ph C═C(CN)₂ H 2234 D2 D2 A1 A1 PhC═C(CN)₂ H 2235 D3 D3 A1 A1 Ph C═C(CN)₂ H 2236 D1 D1 A2 A2 Ph C═C(CN)₂ H2237 D2 D2 A2 A2 Ph C═C(CN)₂ H 2238 D3 D3 A2 A2 Ph C═C(CN)₂ H 2239 D1 D1A3 A3 Ph C═C(CN)₂ H 2240 D2 D2 A3 A3 Ph C═C(CN)₂ H 2241 D3 D3 A3 A3 PhC═C(CN)₂ H 2242 D1 D1 A4 A4 Ph C═C(CN)₂ H 2243 D2 D2 A4 A4 Ph C═C(CN)₂ H2244 D3 D3 A4 A4 Ph C═C(CN)₂ H 2245 D1 D1 A5 A5 Ph C═C(CN)₂ H 2246 D2 D2A5 A5 Ph C═C(CN)₂ H 2247 D3 D3 A5 A5 Ph C═C(CN)₂ H

TABLE 14 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2248 H H H A1 PhC═C(CN)₂ H 2249 H D1 H A1 Ph C═C(CN)₂ H 2250 H D2 H A1 Ph C═C(CN)₂ H2251 H D3 H A1 Ph C═C(CN)₂ H 2252 H H H A2 Ph C═C(CN)₂ H 2253 H D1 H A2Ph C═C(CN)₂ H 2254 H D2 H A2 Ph C═C(CN)₂ H 2255 H D3 H A2 Ph C═C(CN)₂ H2256 H H H A3 Ph C═C(CN)₂ H 2257 H D1 H A3 Ph C═C(CN)₂ H 2258 H D2 H A3Ph C═C(CN)₂ H 2259 H D3 H A3 Ph C═C(CN)₂ H 2260 H H H A4 Ph C═C(CN)₂ H2261 H D1 H A4 Ph C═C(CN)₂ H 2262 H D2 H A4 Ph C═C(CN)₂ H 2263 H D3 H A4Ph C═C(CN)₂ H 2264 H H H A5 Ph C═C(CN)₂ H 2265 H D1 H A5 Ph C═C(CN)₂ H2266 H D2 H A5 Ph C═C(CN)₂ H 2267 H D3 H A5 Ph C═C(CN)₂ H 2268 D1 D1 HA1 Ph C═C(CN)₂ H 2269 D2 D2 H A1 Ph C═C(CN)₂ H 2270 D3 D3 H A1 PhC═C(CN)₂ H 2271 D1 D1 H A2 Ph C═C(CN)₂ H 2272 D2 D2 H A2 Ph C═C(CN)₂ H2273 D3 D3 H A2 Ph C═C(CN)₂ H 2274 D1 D1 H A3 Ph C═C(CN)₂ H 2275 D2 D2 HA3 Ph C═C(CN)₂ H 2276 D3 D3 H A3 Ph C═C(CN)₂ H 2277 D1 D1 H A4 PhC═C(CN)₂ H 2278 D2 D2 H A4 Ph C═C(CN)₂ H 2279 D3 D3 H A4 Ph C═C(CN)₂ H2280 D1 D1 H A5 Ph C═C(CN)₂ H 2281 D2 D2 H A5 Ph C═C(CN)₂ H 2282 D3 D3 HA5 Ph C═C(CN)₂ H 2283 H H H H Ph C═C(CN)₂ H

TABLE 15 Other Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Rs 2284 H H A1 A1 PhC═C(COOH)₂ H 2285 H D1 A1 A1 Ph C═C(COOH)₂ H 2286 H D2 A1 A1 PhC═C(COOH)₂ H 2287 H D3 A1 A1 Ph C═C(COOH)₂ H 2288 H H A2 A2 PhC═C(COOH)₂ H 2289 H D1 A2 A2 Ph C═C(COOH)₂ H 2290 H D2 A2 A2 PhC═C(COOH)₂ H 2291 H D3 A2 A2 Ph C═C(COOH)₂ H 2292 H H A3 A3 PhC═C(COOH)₂ H 2293 H D1 A3 A3 Ph C═C(COOH)₂ H 2294 H D2 A3 A3 PhC═C(COOH)₂ H 2295 H D3 A3 A3 Ph C═C(COOH)₂ H 2296 H H A4 A4 PhC═C(COOH)₂ H 2297 H D1 A4 A4 Ph C═C(COOH)₂ H 2298 H D2 A4 A4 PhC═C(COOH)₂ H 2299 H D3 A4 A4 Ph C═C(COOH)₂ H 2300 H H A5 A5 PhC═C(COOH)₂ H 2301 H D1 A5 A5 Ph C═C(COOH)₂ H 2302 H D2 A5 A5 PhC═C(COOH)₂ H 2303 H D3 A5 A5 Ph C═C(COOH)₂ H 2304 D1 D1 A1 A1 PhC═C(COOH)₂ H 2305 D2 D2 A1 A1 Ph C═C(COOH)₂ H 2306 D3 D3 A1 A1 PhC═C(COOH)₂ H 2307 D1 D1 A2 A2 Ph C═C(COOH)₂ H 2308 D2 D2 A2 A2 PhC═C(COOH)₂ H 2309 D3 D3 A2 A2 Ph C═C(COOH)₂ H 2310 D1 D1 A3 A3 PhC═C(COOH)₂ H 2311 D2 D2 A3 A3 Ph C═C(COOH)₂ H 2312 D3 D3 A3 A3 PhC═C(COOH)₂ H 2313 D1 D1 A4 A4 Ph C═C(COOH)₂ H 2314 D2 D2 A4 A4 PhC═C(COOH)₂ H 2315 D3 D3 A4 A4 Ph C═C(COOH)₂ H 2316 D1 D1 A5 A5 PhC═C(COOH)₂ H 2317 D2 D2 A5 A5 Ph C═C(COOH)₂ H 2318 D3 D3 A5 A5 PhC═C(COOH)₂ H

TABLE 16 Other Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Rs 2319 H H H A1 PhC═C(COOH)₂ H 2320 H D1 H A1 Ph C═C(COOH)₂ H 2321 H D2 H A1 Ph C═C(COOH)₂H 2322 H D3 H A1 Ph C═C(COOH)₂ H 2323 H H H A2 Ph C═C(COOH)₂ H 2324 H D1H A2 Ph C═C(COOH)₂ H 2325 H D2 H A2 Ph C═C(COOH)₂ H 2326 H D3 H A2 PhC═C(COOH)₂ H 2327 H H H A3 Ph C═C(COOH)₂ H 2328 H D1 H A3 Ph C═C(COOH)₂H 2329 H D2 H A3 Ph C═C(COOH)₂ H 2330 H D3 H A3 Ph C═C(COOH)₂ H 2331 H HH A4 Ph C═C(COOH)₂ H 2332 H D1 H A4 Ph C═C(COOH)₂ H 2333 H D2 H A4 PhC═C(COOH)₂ H 2334 H D3 H A4 Ph C═C(COOH)₂ H 2335 H H H A5 Ph C═C(COOH)₂H 2336 H D1 H A5 Ph C═C(COOH)₂ H 2337 H D2 H A5 Ph C═C(COOH)₂ H 2338 HD3 H A5 Ph C═C(COOH)₂ H 2339 D1 D1 H A1 Ph C═C(COOH)₂ H 2340 D2 D2 H A1Ph C═C(COOH)₂ H 2341 D3 D3 H A1 Ph C═C(COOH)₂ H 2342 D1 D1 H A2 PhC═C(COOH)₂ H 2343 D2 D2 H A2 Ph C═C(COOH)₂ H 2344 D3 D3 H A2 PhC═C(COOH)₂ H 2345 D1 D1 H A3 Ph C═C(COOH)₂ H 2346 D2 D2 H A3 PhC═C(COOH)₂ H 2347 D3 D3 H A3 Ph C═C(COOH)₂ H 2348 D1 D1 H A4 PhC═C(COOH)₂ H 2349 D2 D2 H A4 Ph C═C(COOH)₂ H 2350 D3 D3 H A4 PhC═C(COOH)₂ H 2351 D1 D1 H A5 Ph C═C(COOH)₂ H 2352 D2 D2 H A5 PhC═C(COOH)₂ H 2353 D3 D3 H A5 Ph C═C(COOH)₂ H 2354 H H H H Ph C═C(COOH)₂H

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (151). The entire description of WO 2013/011955including the paragraphs 0007 to 0033 and 0059 to 0066 is incorporatedherein by reference.

wherein in the general formula (151), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸each independently represent a hydrogen atom or an electron donatinggroup, provided that at least one thereof represents an electrondonating group; R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ eachindependently represent a hydrogen atom or an electron withdrawinggroup, provided, that, at least one thereof represents an electronwithdrawing group.

Specific examples of the compounds include the compounds shown in thefollowing tables. In the tables, D1 to D10 represent the unsubstitutedelectron donating groups having the following structures, respectively.

TABLE 17

Compound No. R² R⁷ R¹⁰ R¹⁵ Other Rs 3002 D1 D1 CN CN H 3003 D2 D2 CN CNH 3004 D3 D3 CN CN H 3005 D4 D4 CN CN H 3006 D5 D5 CN CN H 3007 D6 D6 CNCN H 3008 D7 D7 CN CN H 3009 D8 D8 CN CN H 3010 D9 D9 CN CN H 3011  D10 D10 CN CN H 3012 H D1 H CN H 3013 H D2 H CN H 3014 H D3 H CN H 3015 HD4 H CN H 3016 H D5 H CN H 3017 H D6 H CN H 3018 H D7 H CN H 3019 H D8 HCN H 3020 H D9 H CN H 3021 H  D10 H CN H

TABLE 18 Compound No. R³ R⁶ R¹¹ R¹⁴ Other Rs 3022 D1 D1 CN CN H 3023 D2D2 CN CN H 3024 D3 D3 CN CN H 3025 D4 D4 CN CN H 3026 D5 D5 CN CN H 3027D6 D6 CN CN H 3028 D7 D7 CN CN H 3029 D8 D8 CN CN H 3030 D9 D9 CN CN H3031 D10 D10 CN CN H 3032 H D1 H CN H 3033 H D2 H CN H 3034 H D3 H CN H3035 H D4 H CN H 3036 H D5 H CN H 3037 H D6 H CN H 3038 H D7 H CN H 3039H D8 H CN H 3040 H D9 H CN H 3041 H D10 H CN H

TABLE 19 Compound No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3042diphenylamino group H CN H H 3043 bis(2-methylphenyl)amino group H CN HH 3044 bis(3-methylphenyl)amino group H CN H H 3045bis(2,4-dimethylphenyl)amino group H CN H H 3046bis(2,6-dimethylphenyl)amino group H CN H H 3047bis(3,5-dimethylphenyl)amino group H CN H H 3048bis(2,4,6-trimethylphenyl)amino group H CN H H 3049bis(4-ethylphenyl)amino group H CN H H 3050 bis(4-propylphenyl)aminogroup H CN H H 3051 diphenylamino group H H CN H 3052bis(2-methylphenyl)amino group H H CN H 3053 bis(3-methylphenyl)aminogroup H H CN H 3054 bis(4-methylphenyl)amino group H H CN H 3055bis(2,4-dimethylphenyl)amino group H H CN H 3056bis(2,6-dimethylphenyl)amino group H H CN H 3057bis(3,5-dimethylphenyl)amino group H H CN H 3058bis(2,4,6-trimethylphenyl)amino group H H CN H 3059bis(4-ethylphenyl)amino group H H CN H 3060 bis(4-propylphenyl)aminogroup H H CN H

TABLE 20 Compound No. R², R⁷ R³, R⁸ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3061 Hdiphenylamino group CN H H 3062 H bis(2-methylphenyl)amino group CN H H3063 H bis(3-methylphenyl)amino group CN H H 3064 Hbis(4-methylphenyl)amino group CN H H 3065 Hbis(2,4-dimethylphenyl)amino group CN H H 3066 Hbis(2,6-dimethylphenyl)amino group CN H H 3067 Hbis(3,5-dimethylphenyl)amino group CN H H 3068 Hbis(2,4,6-trimethylphenyl)amino group CN H H 3069 Hbis(4-ethylphenyl)amino group CN H H 3070 H bis(4-propylphenyl)aminogroup CN H H 3071 H diphenylamino group H CN H 3072 Hbis(2-methylphenyl)amino group H CN H 3073 H bis(3-methylphenyl)aminogroup H CN H 3074 H bis(4-methylphenyl)amino group H CN H 3075 Hbis(2,4-dimethylphenyl)amino group H CN H 3076 Hbis(2,6-dimethylphenyl)amino group H CN H 3077 Hbis(3,5-dimethylphenyl)amino group H CN H 3078 Hbis(2,4,6-trimethylphenyl)amino group H CN H 3079 Hbis(4-ethylphenyl)amino group H CN H 3080 H bis(4-propylphenyl)aminogroup H CN H

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (161). The entire description of WO 2013/081088including the paragraphs 0006 to 0071 and 0118 to 0133 is incorporated,herein by reference.

wherein in the general formula (161), any two or Y¹, Y² and Y³ eachrepresent a nitrogen atom, and the balance thereof represents a methanegroup, of all Y¹, Y² and Y³ each represent a nitrogen atom; Z¹ and Z²each independently represent a hydrogen atom or a substituent; and R¹ toR⁸ each independently represent, a hydrogen atom or a substituent,provided that at least one of R¹ to R⁸ represents a substituted orunsubstituted diarylamino group or a substituted or unsubstitutedcarbazolyl group. The compound represented by the general, formula (161)has at least two carbazole structures in the molecule thereof.

Examples of the compound include the following compounds.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (171). The entire description of JP-A-2013-256490including the paragraphs 0009 to 0046 and 0093 to 0134 is incorporatedherein by reference.

wherein in the general formula (171), Ar¹ to Ar³ each independentlyrepresent a substituted or unsubstituted aryl group, provided that atleast one thereof represents an aryl group substituted by a grouprepresented by the following general formula (172):

wherein in the general formula (172), R¹ to R⁸ each independentlyrepresent, a hydrogen atom or a substituent; Z represents O, S, O═C orAr⁴—N; and Ar⁴ represents a substituted or unsubstituted aryl group,provided that R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, andR⁷ and R⁸ each may be bonded to each other to form a ring structure.

Examples of the compound include the following compounds.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (181). The entire description of JP-A-2013-116975including the paragraphs 0008 to 0020 and 0038 to 0040 is incorporatedherein by reference.

wherein in the general formula (181), R¹, R², R⁴ to R⁸, R¹¹, R¹² and R¹⁴to R¹⁸ each independently represent a hydrogen atom or a substituent.

Examples of the compound include the following compound.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include the following compounds.

(1) A compound represented by the following general formula (191):

wherein in the general formula (191), Ar¹ represents a substituted orunsubstituted arylene group; Ar² and Ar³ each independently represent asubstituted or unsubstituted aryl group; and R¹ to R⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof R¹ to R⁸ represents a substituted or unsubstituted diarylamino group,and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸each may be bonded to each other to form a cyclic structure.

(2) The compound according to the item (1), wherein in the generalformula (191), at least one of R¹ to R⁴ represents a substituted orunsubstituted diarylamino group, and at least, one of R⁵ to R⁸represents a substituted or unsubstituted diarylamino group.

(3) The compound according to the item (2), wherein in the generalformula (191), R³ and R⁶ each represent a substituted or unsubstituteddiarylamino group.

(4) The compound according to any one of the items (1) to (3), whereinin the general formula (191), at least one of R¹ to R⁸ represents asubstituted or unsubstituted diphenylamino group.

(5) The compound according to any one of the items (1) to (4), whereinin the general formula (191), Ar² and Ar³ each independently represent asubstituted or unsubstituted phenyl group.

(6) The compound according to any one of the items (1) to (5), whereinin the general formula (191), Ar¹ represents a substituted orunsubstituted phenylene group, a substituted or unsubstitutednaphthylene group or a substituted or unsubstituted anthracenylenegroup.

(7) The compound according to the item (1), wherein the compound has astructure represented by the following general formula (192):

wherein in the general formula (192), R¹ to R⁸ and R¹¹ to R²⁴ eachindependently represent a hydrogen atom or a substituent, provided thatat least one of R¹ to R⁸ represents a substituted or unsubstituteddiarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶and R⁷, R⁷ and R⁸, R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵,R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and R²⁰, R²¹ and R²², and R²³and R²⁴, each may be bonded to each other to form a ring structure.

(8) The compound according to the item (7), wherein in the generalformula (192), at least one of R¹ to R⁴ represents a substituted orunsubstituted diarylamino group, and at least one of R⁵ to R⁶ representsa substituted or unsubstituted diarylamino group.

(9) The compound according to the item (8), wherein in the generalformula (192), R³ and R⁶ each represent a substituted or unsubstituteddiarylamino group.

Specific examples of the compound include the following compounds. Phrepresents a phenyl group.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include the following compounds.

(1) A compound represented by the following general formula (201):

wherein in the general formula (201), R¹ to R⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof R¹ to R⁸ represents a substituted or unsubstituted carbazolyl group;and Ar¹ to Ar³ each independently represent a substituted orunsubstituted aromatic ring or a heteroaromatic ring.

(2) The compound according to the item (1), wherein in the generalformula (201), at least one of R³ and R⁶ represents a substituted orunsubstituted carbazolyl group.

(3) The compound according to the item (1) or (2), wherein thecarbazolyl group is a 1-carbazolyl group, a 2-carbazolyl group, a3-carbazolyl group or a 4-carbazolyl group.

(4) The compound according to any one of the items (1) to (3), whereinthe carbazolyl group has a substituent on the nitrogen atom in thecarbazole ring structure.

(5) The compound according to any one of the items (1) to (4), whereinin the general formula (201), at least one of Ar¹, Ar² and Ar³represents a benzene ring or a naphthalene ring.

(6) The compound according to any one of the items (1) to (5), whereinin the general formula (201), Ar¹, Ar² and Ar³ each represent the samearomatic ring or the same heteroaromatic ring.

(7) The compound according to any one of the items (1) to (6), whereinin the general formula (201), Ar¹, Ar² and Ar³ each represent a benzenering.

Specific examples of the compound include the following compounds.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formulae (211) and (212). The entire description of WO2013/133359 including the paragraphs 0007 to 0032 and 0079 to 0084 isincorporated herein by reference.

wherein in the general formula (211), Z¹, Z² and Z³ each independentlyrepresent a substituent.

wherein in the general formula (212), Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶each independently represent a substituted or unsubstituted aryl group.

Specific examples of the compound represented by the general formula(212) include the compound represented by the following structuralformula.

Specific examples of the compound represented by the general formula(212) include the compounds shown in the following table. In thecompounds shown in the table, Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are thesame as each other, and are expressed by Ar.

TABLE 21 Compound No. Ar 4002 4-fluorophenyl 4003 3-fluorophenyl 40042-fluorophenyl 4005 3,5-difluorophenyl 4006 2,4,6-trifluorophenyl 40074-methylphenyl 4008 3-methylphenyl 4009 2-methylphenyl 40103,5-dimethylphenyl 4011 2,4,6-trimethylphenyl 4012 4-ethylphenyl 40133-ethylphenyl 4014 2-ethylphenyl 4015 3,5-diethyphenyl 40164-propylphenyl 4017 3-propylphenyl 4018 3,5-dipropylphenyl 40194-tert-butylphenyl 4020 3-tert-butylphenyl 4021 3,5-di-tert-butylphenyl4022 1-naphthyl 4023 2-naphthyl

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (221). The entire description of WO 2013/161437including the paragraphs 0008 to 0054 and 0101 to 0121 is incorporated,herein by reference.

wherein in the general formula (221), R¹ to R¹⁰ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof R¹ to R¹⁰ represents a substituted or unsubstituted aryl group, asubstituted or unsubstituted diarylamino group or a substituted orunsubstituted 9-carbazolyl group, and R¹ and R², R² and R³, R³ and R⁴,R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹⁰each may be bonded to each other to form a ring structure.

Specific examples of the compound include the following compounds.

Examples of the preferred light, emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (231). The entire description of JP-A-2014-9352including the paragraphs 0007 to 0041 and 0060 to 0069 is incorporatedherein by reference.

wherein in the general formula (231), R¹ to R⁴ each independentlyrepresent a hydrogen atom or a substituted or unsubstituted(N,N-diarylamino)aryl group, provided that at least one of R¹ to R⁴represents a substituted or unsubstituted (N,N-diarylamino)aryl group,and two aryl groups constituting the diarylamino moiety of the(N,N-diarylamino)aryl group may be bonded to each other; W¹, W², X¹, X²,Y¹, Y², Z¹ and Z² each independently represent a carbon atom or anitrogen atom; and m¹ to m⁴ each independently represent 0, 1 or 2.

Specific examples of the compound include the following compounds.

Examples of the preferred light emitting material capable of emittingdelayed fluorescent light include compounds represented by the followinggeneral formula (241). The entire description of JP-A-2014-9224including the paragraphs 0008 to 0048 and 0067 to 0076 is incorporatedherein by reference.

wherein in the general formula (241), R¹ to R⁶ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof R¹ to R⁶ represents a substituted or unsubstituted(N/N-diarylamino)aryl group, and two aryl groups constituting thediarylamino moiety of the (N,N-diarylamino)aryl group may be bonded toeach other; X¹ to X⁶ and Y¹ to Y⁶ each independently represent a carbonatom or a nitrogen atom; and n¹, n², p¹, p², q¹ and q² eachindependently represent 0, 1 or 2.

Specific examples of the compound include the following compounds.

Structure of Light Emitting Layer

The structure of the light emitting layer in the organicelectroluminescent device of the invention will be described.

The organic electroluminescent device of the invention uses plural lightemitting materials. The light emitting materials may be containedtogether in one light emitting layer, or may be contained separately indifferent light emitting layers. The organic electroluminescent deviceof the invention may contain a light emitting layer that contain two ormore light emitting materials and a light emitting layer that containsonly one light emitting material.

For example, examples of the structure of the light emitting layers inthe case where two kinds of light emitting materials ere used are shownin FIG. 2. Examples of the two kinds of light emitting materials includea combination of a blue light emitting material and a red light emittingmaterial, and a combination of a blue light emitting material and agreen light emitting material, but the light emitting materials are notlimited to the combinations. It is necessary herein that at least theblue light emitting material that emits light having a short wavelengthis a delayed fluorescent material. In FIG. 2, the numeral 1 denotes alight, emitting material that emits light having the shortestwavelength, and the numeral 2 denotes a light emitting material thatemits light having a longer wavelength. In FIG. 2, the encircled numeralmeans that the light emitting material corresponding to the numeral thatis not encircled is doped with the light emitting material correspondingto the encircled numeral. In FIG. 2, the anode is on the left side, andthe cathode is on the right side.

For example, in the case where a blue light emitting material isselected as the light emitting material 1, and a red light emittingmaterial is selected as the light emitting material 2, the type (1-1) inFIG. 2 means that a light emitting layer formed solely of the blue lightemitting material and a light emitting layer formed solely of the redlight emitting material are formed in this order from the anode side.The type (1-2) shows an embodiment, in which the blue light emittingmaterial is doped with the red light emitting material in one lightemitting layer. Herein, the blue light emitting material functions as alight emitting material that emits fluorescent light containing delayedfluorescent light, and also functions as a host material of the redlight emitting material. The types (1-3) and (1-4) each show anembodiment, in which a light emitting layer formed solely of the bluelight emitting material and a light emitting layer containing the bluelight emitting material doped with the red light emitting material arelaminated. The type (1-5) shows an embodiment, in which a light emittinglayer containing the blue light emitting material doped with the redlight emitting material is laminated between two layers each formedsolely of the blue light emitting material. The invention may use thepatterns of all the embodiments, and preferably uses the types (1-2) to(1-4), and more preferably the type (1-2), from the standpoint of theachievement of a high efficiency with a simple structure.

Examples of the structure of the light emitting layer in the case wherethree kinds of light emitting materials are used are shown in FIGS. 3 to6. Examples of the three kinds of light emitting materials include acombination of a blue light emitting material, a green light emittingmaterial and a red light emitting material, but the light emittingmaterials are not limited to the combination. It is necessary hereinthat at least the blue light emitting material that emits light having ashortest wavelength is a delayed fluorescent material. In FIG. 3, thenumeral 1 denotes a light emitting material that emits light having theshortest wavelength, the numeral 2 denotes a light emitting materialthat emits light having the next shortest wavelength, and the numeral 3denotes a light emitting material that emits light having the longestwavelength. In FIGS. 3 to 6, the encircled numeral means that the lightemitting material corresponding to the numeral that is not encircled isdoped with the light emitting material corresponding to the encirclednumeral. In FIGS. 3 to 6, the anode is on the left side, and the cathodeis on the right side.

The types (2-1) to (2-6) each show an embodiment, in which the threelight emitting materials are solely contained in separate light emittinglayers respectively. Types (3-1) to (3-4) each show an embodiment havinga light emitting layer that contains all the three light emittingmaterials. In the type (3-1) for example, the blue light emittingmaterial functions as a light emitting that emits fluorescent lightcontaining delayed fluorescent light, and also functions as a hostmaterial of the green light emitting material and the red light emittingmaterial. The types (4-1) to (4-14) each show an embodiment having alight emitting layer containing the light emitting material 1 doped withthe light emitting material 2, and a light emitting layer containing thelight emitting material 1 doped with the light emitting material 3. Thetypes (5-1) to (5-9) each show an embodiment having a light emittinglayer containing the light emitting material 2 doped with the lightemitting material 3, and a light emitting layer formed solely of thelight emitting material 1.

In the invention, as represented by the types (3-4) and (4-5) both thelight emitting layer that is the closest to the cathode and the lightemitting layer that is the closest to the anode may be layers that, areformed of the light emitting material that emits light having theshortest wavelength. The light emitting layer containing the lightemitting material that emits light having the shortest wavelength as ahost material may be disposed between the light emitting layer that isthe closest to the cathode and the light emitting layer that the closestto the anode. The structure may provide such an advantage that the lightemission efficiency may be further enhanced.

The types (3-1) to (3-3) are preferably used, and the type (3-1) is morepreferably used, from the standpoint of the achievement of a highefficiency with a simple structure.

The concentration of the light emitting material, with which the lightemitting layer is doped, is preferably 0.01% by weight or more, and morepreferably 0.1% by weight or more, is preferably 50% by weight or less,more preferably 20% by weight or less, and further preferably 10% byweight, or less, and may be, for example 1% by weight or less.

In the case where the light emitting layer is doped with the lightemitting material, the host material may not be the aforementioned lightemitting material. A host material that has been used for an ordinarylight emitting material may be appropriately selected and used. In orderthat the organic electroluminescent device of the invention exhibits ahigh light emission efficiency, it is important that the singletexcitons and the triplet excitons formed in the light emitting materialare confined in the light emitting material. The host material used maybe an organic compound having excited singlet energy and excited tripletenergy, at least one of which is higher than the light emitting materialto be doped. As a result, the singlet excitons and the triplet excitonsformed in the light emitting material can be confined in the molecule ofthe light emitting material, and thereby the light emission efficiencythereof may be sufficiently exploited. However, even though the singletexcitons and the triplet excitons cannot be sufficiently confined, thereare cases where a high light emission efficiency is obtained, andtherefore a host material that is capable of achieving a high lightemission efficiency may be used in the invention without any particularlimitation. In general, the host material preferably an organic compoundthat has a hole transporting function or an electron transportingfunction, prevents the light emission wavelength from being prolonged,and has a high glass transition temperature.

In the organic electroluminescent device of the invention, the lightemission intensity of the light emitting material that emits lighthaving the shortest wavelength is preferably 20% or more, morepreferably 25% or more, and further preferably 30% or more, based on thetotal light emission. In particular, the blue light emission intensityis preferably 20% or more, more preferably 25% or more, and furtherpreferably 30% or more, based on the total light emission.

Structure of Organic Electroluminescent Device

The organic electroluminescent, device of the invention has a structurecontaining at least an anode, a cathode, and one or more organic layersformed between the anode and the cathode. The one or more organic layerscontain a light emitting layer, and may be formed only of a lightemitting layer, or may have one or more organic layers in addition tothe light emitting layer. Examples of the one or more organic layersinclude a hole transporting layer, a hole injection layer, an electronbarrier layer, a hole barrier layer, an electron injection layer, anelectron transporting layer and an exciton barrier layer. The holetransporting layer may be a hole injection and transporting layer havinga hole injection function, and the electron transporting layer may be anelectron injection and transporting layer having an electron injectionfunction. A specific structural example of an organic electroluminescentdevice is shown in FIG. 7. In FIG. 7, the numeral 1 denotes a substrate,2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a holetransporting layer, 5 denotes a light, emitting layer, 6 denotes anelectron transporting layer, 7 denotes an electron injection layer, and8 denotes a cathode.

The members and the layers of the organic electroluminescent device willbe described below. For the light emitting layer, reference may be madeto the aforementioned description relating to the light emitting layer.

Substrate

The organic electroluminescent device of the invention is preferablysupported by a substrate. The substrate is not particularly limited andmay be those that have been commonly used in an organicelectroluminescent device, and examples thereof used include thoseformed of glass, transparent plastics, quartz and silicon.

Anode

The anode of the organic electroluminescent device used is preferablyformed of as an electrode material a metal, an alloy or anelectroconductive compound each having a large work function (4 eV ormore), or a mixture thereof. Specific examples of the electrode materialinclude a metal, such as Au, and an electroconductive transparentmaterial, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A materialthat is amorphous and is capable of forming a transparentelectroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. Theanode may be formed in such a manner that the electrode material isformed into a thin film by such a method as vapor deposition orsputtering, and the film is patterned into a desired pattern by aphotolithography method, or in the case where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In alternative, inthe case where a material capable of being applied as a coating, such asan organic electroconductive compound, is used, a wet film formingmethod, such as a printing method and a coating method, may be used. Inthe case where emitted light is to be taken out through the anode, theanode preferably has a transmittance of more than 10%, and the anodepreferably has a sheet resistance of several hundred ohm per square orless. The thickness thereof may be generally selected from a range offrom 10 to 1,000 nm, and preferably from 10 to 200 nm, while dependingon the material used.

Cathode

The cathode is preferably formed of as an electrode material a metalhaving a small work function (4 eV or less) (referred to as an electroninjection metal), an alloy or an electroconductive compound each havinga small work function (4 eV or less), or a mixture thereof. Specificexamples of the electrode material include sodium, a sodium-potassiumalloy, magnesium, lithium, a magnesium-cupper mixture, amagnesium-silver mixture, a magnesium-aluminum mixture, amagnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture,indium, a lithium-aluminum mixture, and a rare earth metal. Among these,a mixture of an electron injection metal and a second metal that is astable metal having a larger work function than the electron injectionmetal, for example, a magnesium-silver mixture, a magnesium-aluminummixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃)mixture, a lithium-aluminum mixture, and aluminum, are preferred fromthe standpoint of the electron injection property and the durabilityagainst oxidation and the like. The cathode may be produced by formingthe electrode material into a thin film by such a method as vapordeposition or sputtering. The cathode preferably has a sheet resistanceof several hundred ohm per square or less, and the thickness thereof maybe generally selected from a range of from 10 nm to 5 μm, and preferablyfrom 50 to 200 nm. For transmitting the emitted light, any one of theanode and the cathode of the organic electroluminescent device ispreferably transparent or translucent, thereby enhancing the lightemission luminance.

The cathode may be formed with the electroconductive transparentmaterials described for the anode, thereby forming a transparent ortranslucent cathode, and by applying the cathode, a device having ananode and a cathode, both of which have transmittance, may be produced.

Injection Layer

The injection layer is a layer that is provided between the electrodeand the organic layer, for decreasing the driving voltage and enhancingthe light emission luminance, and includes a hole injection layer and anelectron injection layer, which may be provided between the anode andthe light emitting layer or the hole transporting layer and between thecathode and the light emitting layer or the electron transporting layer.The injection layer may be provided depending on necessity.

Barrier Layer

The barrier layer is a layer that is capable of inhibiting charges(electrons or holes) and/or excitons present in the light emitting layerfrom being diffused outside the light emitting layer. The electronbarrier layer may be disposed between the light emitting layer and thehole transporting layer, and inhibits electrons from passing through thelight emitting layer toward the hole transporting layer. Similarly, thehole barrier layer may be disposed between the light emitting layer andthe electron transporting layer, and inhibits holes from passing throughthe light emitting layer toward the electron transporting layer. Thebarrier layer may also be used for inhibiting excitons from beingdiffused outside the light emitting layer. Thus, the electron barrierlayer and the hole barrier layer each may also have a function as anexciton barrier layer. The term “the electron barrier layer” or “theexciton barrier layer” referred herein is intended to include a layerthat has both the functions of an electron barrier layer and an excitonbarrier layer by one layer.

Hole Barrier Layer

The hole barrier layer has the function of an electron transportinglayer in a broad sense. The hole barrier layer has a function ofinhibiting holes from reaching the electron transporting layer whiletransporting electrons, and thereby enhances the recombinationprobability of electrons and holes in the light emitting layer. As thematerial for the hole barrier layer, the materials for the electrontransporting layer described later may be used depending on necessity.

Electron Barrier Layer

The electron barrier layer has the function of transporting holes in abroad sense. The electron barrier layer has a function of inhibitingelectrons from reaching the hole transporting layer while transportingholes, and thereby enhances the recombination probability of electronsand holes in the light emitting layer.

Exciton Barrier Layer

The exciton barrier layer is a layer for inhibiting excitons generatedthrough recombination of holes and electrons in the light emitting layerfrom being diffused to the charge transporting layer, and the use of thelayer inserted enables effective confinement of excitons in the lightemitting layer, and thereby enhances the light emission efficiency ofthe device. The exciton barrier layer may be inserted adjacent to thelight emitting layer on any of the side of the anode and the side of thecathode, and on both the sides. Specifically, in the case where theexciton barrier layer Is present on the side of the anode, the layer maybe inserted between the hole transporting layer and the light emittinglayer and adjacent to the light emitting layer, and in the case wherethe layer is inserted on the side of the cathode, the layer may beinserted between the light emitting layer and the cathode and adjacentto the light emitting layer. Between the anode and the exciton barrierlayer that is adjacent to the light emitting layer on the side of theanode, a hole injection layer, an electron barrier layer and the likemay be provided, and between the cathode and the exciton barrier layerthat is adjacent to the light emitting layer on the side of the cathode,an electron injection layer, an electron transporting layer, a holebarrier layer and the like may be provided. In the case where thebarrier layer is provided, the material used for the barrier layerpreferably has excited singlet energy and excited triplet energy, atleast one of which is higher than the excited singlet energy and theexcited triplet energy of the light emitting material, respectively.

Hole Transporting Layer

The hole transporting layer is formed of a hole transporting materialhaving a function of transporting holes, and the hole transporting layermay be provided as a single layer or plural layers.

The hole transporting material has one of injection or transportingproperty of holes and barrier property of electrons, and may be any ofan organic material and an inorganic material. Examples of known holetransporting materials that may be used herein include a triazolederivative, an oxadiazole derivative, an imidazole derivative, acarbazole derivative, an indolocarbazole derivative, a polyarylalkanederivative, a pyrazoline derivative, a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, an oxazole derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an anilinecopolymer and an electroconductive polymer oligomer, particularly athiophene oligomer. Among these, a porphyrin compound, an aromatictertiary amine compound and a styrylamine compound are preferably used,and an aromatic tertiary amine compound is more preferably used.

Electron Transporting Layer

The electron transporting layer is formed of a material having afunction of transporting electrons, and the electron transporting layermay be provided as a single layer or plural layers.

The electron transporting material (which may also function as a holebarrier material in some cases) needs only to have a function oftransporting electrons, which are injected from the cathode, to thelight emitting layer. Examples of the electron transporting layer thatmay be used herein include a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethaneand anthrone derivatives, and an oxadiazole derivative. The electrontransporting material used may be a thiadiazole derivative obtained byreplacing the oxygen atom of the oxadiazole ring of the oxadiazolederivative by a sulfur atom, or a quinoxaline derivative having aquinoxaline ring, which is known as an electron attracting group.Furthermore, polymer materials having these materials introduced to thepolymer chain or having these materials used as the main chain of thepolymer may also be used.

In the production of the organic electroluminescent device, the compoundrepresented by the general formula (1) not only may be used in the lightemitting layer, but also may be used in the other layers than the lightemitting layer. In this case, the compound represented by the generalformula (1) used in the light emitting layer and the compoundrepresented by the general formula (1) used in the other layers than thelight emitting layer may be the same as or different from each other.For example, the compound represented by the general formula (1) may beused in the injection layer, the barrier layer, the hole barrier layer,the electron barrier layer, the exciton barrier layer, the holetransporting layer, the electron transporting layer and the likedescribed above. The film forming method of the layers are notparticularly limited, and the layers may be produced by any of a dryprocess and a wet process.

Specific examples of preferred materials that may be used in the organicelectroluminescent device are shown below, but the materials that may beused in the invention are not construed as being limited to the examplecompounds. The compound that is shown as a material having a particularfunction may also be used as a material having another function. In thestructural formulae of the example compounds, R, R′ and R₁ to R₁₀ eachindependently represent a hydrogen atom or a substituent, X represents acarbon atom or a hetero atom constituting the ring skeleton, nrepresents an integer of from 3 to 5, Y represents a substituent, and mrepresents an integer of 0 or more.

Preferred examples of a compound that may be used as the host materialof the light emitting layer are shown below.

Preferred examples of a compound that may be used as the hole injectionmaterial are shown below.

Preferred examples of a compound that may be used as the holetransporting material are shown below.

Preferred examples of a compound that may be used as the electronbarrier material are shown below.

Preferred examples of a compound that may be used as the hole barriermaterial are shown below.

Preferred examples of a compound that may be used as the electrontransporting material are shown below.

Preferred examples of a compound that may be used as the electronInjection material are shown below.

Preferred examples of a compound as a material that may be added areshown below. For example, the compound may be added as a stabilizingmaterial.

The organic electroluminescent device thus produced by theaforementioned method emits light on application of an electric fieldbetween the anode and the cathode of the device. In this case, when thelight emission is caused by the excited single energy, light having awavelength that corresponds to the energy level thereof may be confirmedas fluorescent light and delayed fluorescent light. When the lightemission is caused by the excited triplet energy, light hawing awavelength that corresponds to the energy level thereof may be confirmedas phosphorescent light. The normal fluorescent light has a shorterlight emission lifetime than the delayed fluorescent light, and thus thelight emission lifetime may be distinguished between the fluorescentlight and the delayed fluorescent light.

The organic electroluminescent device of the invention may be applied toany of a single device, a structure with plural devices disposed in anarray, and a structure having anodes and cathodes disposed in an X-Ymatrix. According to the invention, an organic light emitting devicethat is largely improved in light emission efficiency may be obtained.The organic light emitting device, such as the organicelectroluminescent device, of the invention may be applied to a furtherwide range of purposes. For example, an organic electroluminescentdisplay apparatus may be produced with the organic electroluminescent,device of the invention, and for the details thereof, reference may bemade to S. Tokito, C. Adachi and H. Murata, “Yuki EL Display” (OrganicEL Display) (Ohmsha, Ltd.). In particular, the organicelectroluminescent device of the invention may be applied to organicelectroluminescent illumination and backlight which are highly demanded.

EXAMPLE

The features of the invention will be described more specifically withreference to examples below. The materials, processes, procedures andthe like shown below may be appropriately modified unless they deviatefrom the substance of the invention. Accordingly, the scope of theinvention is not construed as being limited to the specific examplesshown below. The organic, electroluminescent devices were measured byusing Semiconductor Parameter Analyzer (E5273A, produced by AgilentTechnologies, Inc.), Optical Power Meter (1930C, produced by NewportCorporation) and Fiber Optic Spectrometer (USB2000, produced by OceanOptics, Inc.).

Test Example 1

The difference (ΔE_(ST)) between the singlet energy (E_(S1)) and thetriplet energy (E_(T1)) of the light emitting materials used in thefollowing examples was obtained in such a manner that the singlet energy(E_(S1)) and the triplet energy (E_(T1)) were measured in the followingmanners, and the difference (ΔE_(ST)) was obtained by the expression,ΔE_(ST)=E_(S1)−E_(T1). The measurement results are shown in Table 22.

(1) Singlet Energy E_(S1)

The compound to be measured and DPEPO were vapor-co-deposited to athickness of 100 nm on a Si substrate to make a concentration of thecompound to be measured of 6% by weight, which was designated as aspecimen. The specimen was measured for a fluorescent spectrum atordinary temperature (300 K). The light emission was accumulated fromimmediately after the incidence of excitation light to 100 nsec afterthe incidence, thereby providing a fluorescent, spectrum with thefluorescence intensity as the ordinate and the wavelength as theabscissa. In the fluorescent spectrum, the ordinate is the lightemission, and the abscissa is the wavelength. A tangent line was drawnfor the downfalling part of the light emission spectrum on the shortwavelength side, and the wavelength λedge (nm) of the intersection pointof the tangent line and the abscissa was obtained. The wavelength valuewas converted to an energy value according to the following conversionexpression to provide the singlet energy E_(S1).E _(S1) (eV)=1239.85/λedge  Conversion Expression

The light emission spectrum was measured with a nitrogen laser (MNL200,produced by Lasertechnik Berlin GmbH) as an excitation light source anda streak camera (C4334, produced by Hamamatsu Photonics K.K.) as adetector.

(2) Triplet Energy E_(T1)

The same specimen as used for the singlet energy E_(S1) was cooled to 5K, the specimen for measuring phosphorescent light was irradiated withexcitation light (337 nm), and the phosphorescence intensity wasmeasured with a streak camera. The light emission was accumulated from 1msec after the incidence of excitation light to 10 msec after theincidence of excitation light, thereby providing a phosphorescentspectrum with the phosphorescence intensity as the ordinate and thewavelength as the abscissa. A tangent line was drawn for the upstandingpart of the phosphorescent spectrum on the short wavelength side, andthe wavelength λedge (nm) of the intersection point of the tangent lineand the abscissa was obtained. The wavelength value was converted to anenergy value according to the following conversion expression to providethe singlet energy E_(T1).E _(T1) (eV)=1239.85/λedge  Conversion Expression

The tangent line for the upstanding part of the phosphorescent spectrumon the short wavelength side was drawn in the following manner. Over therange in the phosphorescent spectrum curve of from the short wavelengthend to the maximum peak value closest to the short wavelength end amongthe maximum peak values of the spectrum, a tangent line was assumedwhile moving within the range toward the long wavelength side. Thegradient of the tangent line was increased while the curve was standingup (i.e., the value of the ordinate was increased). The tangent linethat was drawn at the point where the gradient thereof became maximumwas designated as the tangent line for the upstanding part of thephosphorescent spectrum on the short wavelength side.

A maximum peak having a peak intensity that was 10% or less of themaximum peak point intensity of the spectrum was not included in themaximum peak values and thus was not designated as the maximum peakvalue closest to the short wavelength end, and the tangent line that wasdrawn, at the point where the gradient became maximum that was closestto the maximum peak, value closest to the short wavelength end wasdesignated as the tangent line for the upstanding part of thephosphorescent spectrum on the short wavelength side.

TABLE 22 Light emitting material ΔE_(ST) (eV) ZHS02 0.22 2CzPN 0.254CzIPN 0.11 4CzTPN-Ph 0.06

Example 1

In this example, a multiple wavelength light emitting organic,electroluminescent device containing light emitting materials of threecolors, i.e., a blue light emitting material, a green light emittingmaterial and a red light emitting material, that were mixed in one lightemitting layer was produced and evaluated.

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 100 nm, bya vacuum vapor deposition method at a vacuum degree of 5×10⁻⁴ Pa orless. Firstly, α-NPD was formed to a thickness of 35 nm on ITO, andthereon mCBP was formed to a thickness of 10 nm. ZHS02 as a blue lightemitting material, 4CzIPN as a green light emitting material and4CzTPN-Ph as a red light emitting material were vapor-co-deposited fromseparate vapor deposition sources to form a layer having a thickness of15 nm, which was designated as a light emitting layer. At this time, theconcentrations of 4CzIPN and 4CzTPN-Ph each were 0.1% by weight, and thebalance was ZHS02. PPT was then formed to a thickness of 10 nm, TPBi wasformed to a thickness of 40 nm, then lithium fluoride (LiF) was vacuumvapor-deposited to a thickness of 0.8 nm, and then aluminum (Al) wasvapor-deposited to a thickness of 100 nm to form a cathode, therebyproducing an organic electroluminescent device.

The light emission spectrum of the organic electroluminescent devicethus produced is shown in FIG. 8, the electric current density-externalquantum efficiency characteristics thereof are shown in FIG. 9, and theenergy band diagram thereof is shown in FIG. 10. The external quantumefficiency and the chromaticity thereof thus obtained were as shown inTable 23. The light emission intensity ratio was 32% for blue lightemission, 49% for green light emission and 19% for red light emission.The intensity ratio of blue light emission was enhanced by the bluedelayed fluorescent light, and thereby both favorable blue color and ahigh light emission efficiency were simultaneously achieved.

Examples 2 to 4

In these examples, multiple wavelength light emitting organicelectroluminescent devices each containing light emitting materials oftwo colors, i.e., a blue light emitting material and a red lightemitting material, that were mixed in one light emitting layer at threedifferent concentrations were produced and evaluated.

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 100 nm, bya vacuum vapor deposition method at a vacuum degree of 5×10−4 Pa orless. Firstly, α-NPD was formed to a thickness of 35 nm on ITO, andthereon mCBP was formed to a thickness of 10 nm. 2CzPN as a blue lightemitting material and 4CzTPN-Ph as a red light emitting material werevapor-co-deposited from separate vapor deposition sources to form alayer having a thickness of 15 nm, which was designated as a lightemitting layer. At this time, the concentration of 4CzTPS-Ph was 0.1% byweight (Example 2), 0.2% by weight (Example 3) or 0.5% by weight(Example 4). TmPyPb was then formed to a thickness of 50 nm, thenlithium fluoride (LiF) was vacuum vapor-deposited to a thickness of 0.8nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nmto form a cathode, thereby producing an organic electroluminescentdevice.

The light emission spectra of the organic electroluminescent devicesthus produced are shown in FIG. 11, the electric currentdensity-external quantum efficiency characteristics thereof are shown inFIG. 12, and the energy band diagram thereof is shown in FIG. 13. Theexternal quantum efficiency and the chromaticity thereof thus obtainedwere as shown in Table 23. Both favorable blue color and a high lightemission efficiency were simultaneously achieved.

Example 5

In this example, a multiple wavelength, light emitting organicelectroluminescent device having a light emitting layer containing ablue light emitting material doped with a red light emitting materialthat was held between light emitting layers each formed only of a bluelight emitting material was produced and evaluated.

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 100 nm, bya vacuum vapor deposition method at a vacuum degree of 5×10⁻⁴ Pa orless. Firstly, α-NPD was formed to a thickness of 35 nm on ITO, thenmCBP was formed thereon to a thickness of 10 nm, and ZHS02 as a bluelight emitting material was formed to a thickness of 7 nm. ZHS02 and4CzTPN-Ph as a red light emitting material were vapor-co-deposited fromseparate vapor deposition sources to form a layer having a thickness of1 nm, which was designated as a light emitting layer. At this time, theconcentration of 4CzTPN-Ph was 0.2% by weight. ZHS02 was then formed toa thickness of 7 nm, TmPyPb was formed to a thickness of 50 nm, thenlithium fluoride (LiF) was vacuum vapor-deposited to a thickness of 0.8nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nmto form a cathode, thereby producing an organic electroluminescentdevice.

The light emission spectrum of the organic electroluminescent devicethus produced is shown in FIG. 14, the electric current density-externalquantum efficiency characteristics thereof are shown in FIG. 15, and theenergy band diagram thereof is shown in FIG. 16. The external quantumefficiency and the chromaticity thereof thus obtained were as shown inTable 23. Both favorable blue color and a high light emission efficiencywere simultaneously achieved.

TABLE 23 Maximum External external quantum Voltage quantum efficiency at10 at 10 efficiency mA/cm² mA/cm² (%) (%) (V) Chromaticity Example 1 9.53.4 9 0.28, 0.41 Example 2 9.7 4.0 8 0.36, 0.51 Example 3 11.1 6.5 70.42, 0.50 Example 4 10.5 7.8 7.8 0.47, 0.49 Example 5 10.77 5.5 7 0.37,0.51

Examples 6 to 8

In these examples, multiple wavelength light emitting organicelectroluminescent devices each containing a blue light emittingmaterial, a green light emitting material and a red light emittingmaterial that were all delayed fluorescent materials were produced andevaluated.

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 100 nm, bya vacuum vapor deposition method at a vacuum degree of 5×10⁻⁴ Pa orless. Firstly, HATCN was formed to a thickness of 10 nm on ITO, andthereon TrisPCz was formed to a thickness of 35 nm. PXZ-TRZ as a greenlight emitting material and mCBP were vapor-co-deposited from separatevapor deposition sources to form a layer having a thickness of 6 nm,which was designated as a first light emitting layer (the concentrationof PXZ-TRZ was 10% by weight). Subsequently, PXZ-TRZ, 4CzTPN-Ph as a redlight emitting material, and mCBP were vapor-co-deposited from separatevapor deposition sources to form a layer having a thickness of 3 nm,which was designated as a second light emitting layer (the concentrationof PXZ-TRZ was 6% by weight, and the concentration of 4CzTPN-Ph was 2%by weight). SHT02 as a blue light emitting material and DPEPO werevapor-co-deposited from separate vapor deposition sources to form alayer having a thickness of 6 nm, which was designated as a third lightemitting layer (the concentration of SHT02 was 6% by weight). DPEPO wasthen formed to a thickness of 10 nm, and TmPyPb was formed to athickness of 40 nm. Lithium fluoride (LiF) was vacuum vapor-deposited toa thickness of 0.6 nm, and then aluminum (Al) was vapor-deposited to athickness of 100 nm to form a cathode, thereby producing an organicelectroluminescent device A (Example 6).

An organic electroluminescent device B was produced in the sameproduction process as the organic electroluminescent device A exceptthat a PPT layer having a thickness of 10 nm was formed instead of theDPEPO layer having a thickness of 10 nm (Example 7).

An organic electroluminescent device C was produced in the sameproduction process as the organic electroluminescent device A exceptthat the DPEPO layer having a thickness of 10 nm was not formed (Example8).

The light emission spectra of the organic electroluminescent device Athus produced are shown in FIG. 17. The chromaticity thereof was 0.31,0.36. The voltage-electric current density characteristics of theorganic electroluminescent devices A to C are shown in FIG. 18, theelectric current density-external quantum efficiency characteristicsthereof are shown in FIG. 19, and the energy band diagram thereof isshown in FIG. 20. The organic electroluminescent devices A to Cexhibited favorable light emission characteristics as a white lightemitting device, and the organic electroluminescent device A achieved anexternal quantum efficiency of 11.8%.

Examples 9 to 11

In these examples, multiple wavelength light emitting organicelectroluminescent devices each containing a blue light, emittingmaterial, a green light emitting material and a red light emittingmaterial that were all delayed fluorescent materials with the use ofanother green light emitting material were produced and evaluated.

Organic electroluminescent devices D to F were produced in the sameproduction process as the organic electroluminescent device A in Example6 except that 4CzPN was used as a green light emitting material insteadof PXZ-TRZ, and the thicknesses of the first light emitting layer, thesecond light emitting layer and the third light emitting layer werechanged as follows.

Device D: first light emitting layer (6 nm), second light emitting layer(3 nm), third light emitting layer (6 nm)

Device E: first light emitting layer (4 nm), second light emitting layer(3 nm), third light emitting layer (8 nm)

Device F: first light emitting layer (3 nm), second light emitting layer(2 nm), third light emitting layer (15 nm)

The light emission spectra of the organic electroluminescent devices Dto F thus produced are shown in FIG. 21. The chromaticity of the organicelectroluminescent light emitting device F was 0.30, 0.39. Thevoltage-electric current density characteristics of the organicelectroluminescent devices D to F are shown in FIG. 22, and the electriccurrent density-external quantum efficiency characteristics thereof areshown in FIG. 23. The organic electroluminescent device F exhibitedfavorable light emission characteristics as a white light emittingdevice and achieved an external, quantum efficiency of 12.1%.

INDUSTRIAL APPLICABILITY

The organic electroluminescent device of the invention is designed insuch a manner that in the light emitted from the plural light emittingmaterials contained in the device, the light that has the shortestwavelength contains delayed fluorescent light. According to the design,the color tone of the device is improved through the enhancement of thelight emission efficiency of light having a relatively short wavelength,such as blue light. The organic electroluminescent device of theinvention has a large degree of freedom in design to achieve a simplestructure, and thereby the intended multiple wavelength light emittingorganic electroluminescent device may be produced. Therefore, theinvention has high industrial applicability.

REFERENCE SIGNS LIST

-   1 substrate-   2 anode-   3 hole injection layer-   4 hole transporting layer-   5 light emitting layer-   6 electron transporting layer-   7 electron injection layer-   8 cathode

The invention claimed is:
 1. An organic electroluminescent devicecontaining a cathode, an anode, and one or more organic layers thatinclude at least one light emitting layer containing plural lightemitting materials between the cathode and the anode, provided that whentwo or more light emitting layers exist, they are laminated to eachother, wherein the organic electroluminescent device is a multiplewavelength light emitting organic electroluminescent device emittinglight from the plural light emitting materials, which satisfies thefollowing A, B and C: A. all light emitting materials contained in thelayers between the cathode and anode are fluorescent materials, B. inthe light thus emitted from the light emitting materials, light that hasthe shortest wavelength contains delayed fluorescent light, and C. thelight emitting material that emits light having the shortest wavelengthalso functions as a host material of another light emitting material; orone of the organic layers consists of only the material that emits lighthaving the shortest wavelength.
 2. The organic electroluminescent deviceaccording to claim 1, wherein the light emitting material that emitslight having the shortest wavelength has an energy difference (ΔE_(ST))between the lowest excitation triplet energy level and the lowestexcitation singlet energy level at 5 L of 0.3 eV or less.
 3. The organicelectroluminescent device according to claim 1, wherein the lightemitting material that emits light having the shortest wavelength is ablue light emitting material.
 4. The organic electroluminescent deviceaccording to claim 1, wherein the light emitting material that emitslight having the shortest wavelength has a light emission intensity ofmore than 20% based on the total light emission.
 5. The organicelectroluminescent device according to claim 1, wherein one of theorganic layers contains the light emitting material that emits lighthaving the shortest wavelength and at least one kind of a light emittingmaterial that emits light having a different wavelength, and the lightemitting material that emits light having the shortest wavelength alsofunctions as a host material.
 6. The organic electroluminescent deviceaccording to claim 1, wherein one of the organic layers contains thelight emitting material that emits light having the shortest wavelengthand at least two kinds of light emitting materials that each emit lighthaving a different wavelength, and the light emitting material thatemits light having the shortest wavelength also functions as a hostmaterial.
 7. The organic electroluminescent device according to claim 1,wherein one of the organic layers consists of only the material thatemits light having the shortest wavelength.
 8. The organicelectroluminescent device according to claim 1, wherein the organicelectroluminescent device contains two or more layers each containing alight emitting material, and among the layers, a layer that is theclosest to the cathode and a layer that is the closest to the anode eachcontain the light emitting material that emits light having the shortestwavelength.
 9. The organic electroluminescent device according to claim8, wherein the organic electroluminescent device contains a layer thatcontains the light emitting material that emits light having theshortest wavelength as a host material between the layer that is theclosest to the cathode and the layer that is the closest to the anode.10. The organic electroluminescent device according to claim 1, whereinthe organic electroluminescent device contains a layer containing a bluelight emitting material doped with a green light emitting material or ared light emitting material.
 11. The organic electroluminescent deviceaccording to claim 1, wherein the organic electroluminescent devicecontains a laminate of a layer containing a blue light emittingmaterial, a layer containing a blue light emitting material doped with agreen light emitting material or a red light emitting material, and alayer containing a blue light emitting material.
 12. The organicelectroluminescent device according to claim 1, wherein the plural lightemitting materials contain a blue light emitting material, a green lightemitting material, and a red light emitting material.
 13. The organicelectroluminescent device according to claim 1, wherein the organicelectroluminescent device contains a layer containing a blue lightemitting material doped with a green light emitting material and a redlight emitting material.
 14. The organic electroluminescent deviceaccording to claim 1, wherein the organic electroluminescent devicecontains a laminate of a layer containing a green light emittingmaterial, a layer containing a green light emitting material doped witha red light emitting material, and a layer containing a blue lightemitting material.
 15. The organic electroluminescent device accordingto claim 1, wherein all the plural light emitting materials emit delayedfluorescent light.
 16. The organic electroluminescent device accordingto claim 1, wherein the organic electroluminescent device emits whitelight through color mixing of light emitted from the plural lightemitting materials.
 17. The organic electroluminescent device accordingto claim 1, wherein the light emitting material that emits light havingthe shortest wavelength also functions as a host material of anotherlight emitting material; or one of the organic layers consists of onlythe material that emits light having the shortest wavelength and amongthe layers containing a light emitting material, a layer that is theclosest to the anode is a layer containing the light emitting materialthat emits light having the shortest wavelength.